Pyridine → Cyclohexanone, 4-[(acetyloxy)methyl]-4-(4-chlorophenyl)-

HRID 1576217Notes

Reaction equation

HRID 1576217 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>O>[C:23]([O:1][CH2:2][C:3]1([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 215146584-(4-Chlorophenyl)-4-(hydroxymethyl)cyclohexan-1-one

Product 1

HCID 12230249Cyclohexanone, 4-[(acetyloxy)methyl]-4-(4-chlorophenyl)-Yield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-hydroxymethyl-4-(4-chlorophenyl)cyclohexanone is dissolved in 60 ml. of pyridine and 30 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, sodium bicarbonate solution and brine, and evaporated to dryness to give 12.8 g. (66% yield) of 4-acetoxymethyl-4-(4-chlorophenyl)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, sodium bicarbonate solution and brine
  4. customevaporated to dryness
  5. customto give 12.8 g

Sources & evidence

ORD record
ord-cce86f7717ce486caf8f3b7c5480f6b1
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

Loading…