Pyridine → [1-(3,4-Dimethoxyphenyl)-4-oxocyclohexyl]methyl acetate

HRID 1576220Notes

Reaction equation

HRID 1576220 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O>[C:26]([O:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 215146714-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one

Product 1

HCID 21514706[1-(3,4-Dimethoxyphenyl)-4-oxocyclohexyl]methyl acetateYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-hydroxymethyl-4-(3,4-dimethoxyphenyl)cyclohexanone is dissolved in 20 ml. of pyridine and 10 ml. of acetic anhydride. After about 20 hours of standing at room temperature, the mixture is poured into ice and water. The gum that precipitates is extracted with ether. The organic layer is washed successively with water, 2.5 N hydrochloric acid, water and brine, and evaporated to dryness to give 6.43 g. (57% yield) of 4-acetoxymethyl-4-(3,4-dimethoxyphenyl)cyclohexanone, as an amorphous gum.

Workup

  1. customThe gum that precipitates
  2. extractionis extracted with ether
  3. washThe organic layer is washed successively with water, 2.5 N hydrochloric acid, water and brine
  4. customevaporated to dryness
  5. customto give 6.43 g

Sources & evidence

ORD record
ord-4393d21c72bb42839169441d1910a593
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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