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Process for the preparation of aromatic alpha-hydroxy ketones

A technology for hydroxy ketones and aromatic ketones, applied in the field of preparing aromatic α-hydroxy ketones, can solve the problems of not finding aromatic α-hydroxy ketones and the like

Inactive Publication Date: 2011-04-13
LAMBERTI SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] A method for the preparation of aromatic α-hydroxy ketones that does not require the use of chlorinated solvents or any other solvents or chlorine, sulfonyl chloride and bromine has not been found

Method used

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  • Process for the preparation of aromatic alpha-hydroxy ketones
  • Process for the preparation of aromatic alpha-hydroxy ketones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Preparation of 2-Hydroxy-2-methyl-propiophenone

[0068] a) Acylation

[0069] -Synthesis of 2-methyl-propiophenone (isobutyrophenone)

[0070] 123 g of aluminum chloride (1.02 mol) was added portionwise to a solution of 120 g of benzene (1.53 mol) and 108.2 g of isobutyryl chloride (1.02 mol) over 2 hours while stirring and maintaining the temperature at 5 °C . The mixture was kept under stirring for another 1 hour without cooling. By TLC (SiO 2 , toluene) detection reaction. The mixture was poured into ice with stirring. The organic layer was separated, the solvent was evaporated under vacuum, and the product was distilled at 163 °C and 160 mmHg to obtain 140 g of a colorless oil (95% yield), which was used in the next step.

[0071] b) Halogenation

[0072] - Synthesis of 2-chloro-2-methyl-propiophenone (method A)

[0073] At 40°C, 31 g of a 12% aqueous solution of NaClO (0.05 mol) was added dropwise in 90' to 7.4 g of 2-methyl-propiophenone (0.05 mol) obtain...

Embodiment 2

[0081] Preparation of 2-Hydroxy-1-{3-[4-(2-Hydroxy-2-methyl-propionyl)-phenyl]-1,1,3-trimethyl-indan-5-yl}-2 -Methyl-propan-1-one and 2-hydroxy-1-{1-[4-(2-hydroxy-2-methyl-propionyl)-phenyl]-1,3,3-trimethyl- Mixture of indan-5-yl}-2-methyl-propan-1-one

[0082] a) Acylation

[0083] - Synthesis of 1-[4-(5-isobutyryl-1,3,3-trimethyl-indan-1-yl)-phenyl]-2-methyl-propan-1-one and 1-[ Mixture of 4-(6-isobutyryl-1,3,3-trimethyl-indan-1-yl)-phenyl]-2-methyl-propan-1-one

[0084] With stirring and keeping the temperature at 25°C, 14.66 g of aluminum chloride (110 mol) was added portionwise to 11.82 g of 1,3,3-trimethyl-1-phenyl-indane ( 50 mmol) and 13.38 g of isobutyryl chloride (123 mmol). The mixture was heated with stirring and maintained at 60° C. for a further hour; the viscosity of the mixture increased. By TLC (SiO 2 , toluene) detection reaction. The mixture was treated with 112 g of hydrochloric acid (4%) without exceeding 80°C. At 60°C, the organic layer was separa...

Embodiment 3

[0095] Preparation of 2-Hydroxy-1-{4-[4-(2-Hydroxy-2-methyl-propionyl)-phenoxy}-2-methyl-1-propan-1-one.

[0096] a) Acylation

[0097] - Synthesis of 1-[4-(4-isobutyryl-phenoxy)-phenyl]-2-methyl-propan-1-one

[0098] While stirring and keeping the temperature between 5°-15°C, 15.33 g of aluminum chloride (115 mmol) was added in portions to 8.6 g of diphenyl ether (50 mmol) and 11.97 g of in a solution of isobutyryl chloride (110 mmol). The mixture was kept under stirring at 15°C for a further 1 hour, then heated at 50°C for 1 hour. The mixture was treated with 100 ml of water with stirring. The organic layer was separated to give 11 g of a yellow oil which was used in the next step without purification. The sample was crystallized from petroleum ether at 40°-65°C to obtain a slightly white solid with a melting point of 54°C.

[0099] H1NMR (300MHz, CDCl 3 ): δ: 7.98 (d, 4H); 7.04 (d, 4H); 3.45-3.55 (m, 2H); 1.21 (d, 12H).

[0100] b) Halogenation

[0101] - Synthesis ...

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Abstract

Process for the preparation of aromatic alpha-hydroxyketones (aromatic a- hydroxyketones) that does not require the use of chlorine, sulfuryl chloride or bromine and comprises the halogenation of an intermediate aromatic ketone with a hydrogen halide in the presence of an oxidising compound.

Description

field of invention [0001] The present invention relates to a process for the preparation of aromatic alpha-hydroxy ketones which does not require the use of chlorine, sulfonyl chloride or bromine. technical background [0002] As used herein, the term "aromatic alpha-hydroxyketone" refers to a ketone having the following characteristics: one substituent on the carbonyl carbon atom is an aryl group, and the other substituent is an alkyl group on the carbon atom immediately adjacent to the carbonyl group Contains hydroxyl (-OH). [0003] Aromatic α-hydroxyketones are widely used as photoinitiators. A more general synthetic route to aromatic α-hydroxyketones involves key intermediates α-haloketones. [0004] As reported in EP 3002 and WO 2004099111, α-haloketones are prepared by reacting alkylaryl ketones with chlorine, bromine or sulfonyl chlorides, which leads to the corresponding α-haloalkylaryl ketones: the reported methods also Requires the use of halogenated organic so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36C07C45/46C07C49/80C07C49/813
CPCC07C45/46C07C45/36C07C49/813C07C49/80
Inventor E·梅内古佐G·诺西尼G·利巴希
Owner LAMBERTI SPA
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