Water → 2-Acetyl-6-methylphenyl cyclohexanecarboxylate

HRID 1200179Notes

Reaction equation

HRID 1200179 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11])(=[O:3])[CH3:2].[CH:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.O>N1C=CC=CC=1>[CH:12]1([C:18]([O:11][C:5]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=2[C:1](=[O:3])[CH3:2])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 75938Cyclohexanecarbonyl chlorideHCID 2404371-(2-Hydroxy-3-methylphenyl)ethan-1-one

Product 1

HCID 146504262-Acetyl-6-methylphenyl cyclohexanecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Acetyl-6-methylphenol (3.0 g) was dissolved in pyridine (15 ml) and to the solution was added dropwise cyclohexanecarbonyl chloride (3.08 g) with stirring at room temperature. After stirring for 4 hours, the reaction mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with water, diluted hydrochloric acid and then water and dried (MgSO4). The solvent was distilled off under reduced pressure to obtain the title compound (5.2 g) as oil in a quantitative yield.

Workup

  1. stirringAfter stirring for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, diluted hydrochloric acid
  4. dry with materialwater and dried (MgSO4)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0ef8405afcfb469ca191977d2c75a562
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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