Pyridine → (4-Oxo-1-phenylcyclohexyl)methyl acetate

HRID 1576216Notes

Reaction equation

HRID 1576216 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>O>[C:22]([O:1][CH2:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 215146764-(Hydroxymethyl)-4-phenylcyclohexan-1-one

Product 1

HCID 21514685(4-Oxo-1-phenylcyclohexyl)methyl acetateYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.6 g. of 4-hydroxymethyl-4-phenylcyclohexanone is dissolved in 40 ml. of pyridine and 20 ml. 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 then evaporated to dryness. The solid residue is recrystallized from Skellysolve B to give 6.74 g. (35.8% yield) of 4-acetoxymethyl-4-phenylcyclohexanone, having a melting point of 74° to 79°C.

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. customThe solid residue is recrystallized from Skellysolve B
  6. customto give 6.74 g

Sources & evidence

ORD record
ord-ebf73aacd42445a5a9b53afbcc3f23c5
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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