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

HRID 1576218Notes

Reaction equation

HRID 1576218 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([F: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]([F: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 215147454-(4-Fluorophenyl)-4-(hydroxymethyl)cyclohexan-1-one

Product 1

HCID 12230250Cyclohexanone, 4-[(acetyloxy)methyl]-4-(4-fluorophenyl)-Yield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-hydroxymethyl-4-(4-fluorophenyl)cyclohexanone is dissolved in 50 ml. of pyridine and 30 ml. of acetic anhydride. After about 20 hours of standing at room temperature, the mixture is pured into ice and water. The gum that precipitates is extracted with ether. The organic layer is washed sucessively with water, 2.5 N hydrochloric acid, water, sodium bicarbonate solution and brine, and evaporated to dryness. The solid residue is recrystallized from ether to give 9.77 g. (57% yield) of 4-acetoxymethyl-4-(4-fluorophenyl)cyclohexanone, having a melting point of 80° to 84°C.

Workup

  1. customThe gum that precipitates
  2. extractionis extracted with ether
  3. washThe organic layer is washed sucessively with water, 2.5 N hydrochloric acid, water, sodium bicarbonate solution and brine
  4. customevaporated to dryness
  5. customThe solid residue is recrystallized from ether
  6. customto give 9.77 g

Sources & evidence

ORD record
ord-78a3f4c3d35b4119bed58d6d724be460
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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