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

HRID 1576219Notes

Reaction equation

HRID 1576219 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>O>[C:24]([O:1][CH2:2][C:3]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 215147324-(Hydroxymethyl)-4-(4-methoxyphenyl)cyclohexan-1-one

Product 1

HCID 12230251Cyclohexanone, 4-[(acetyloxy)methyl]-4-(4-methoxyphenyl)-Yield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-hydroxymethyl-4-(4-methoxyphenyl)cyclohexanone is dissolved in 12 ml. of pyridine and 6 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. The solid residue is recrystallized from a mixture of ether and Skellysolve B to give 2.95 g. (68% yield) of 4-acetoxymethyl-4-(4-methoxyphenyl)cyclohexanone, having a melting point of 86.5° to 88°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 a mixture of ether and Skellysolve B
  6. customto give 2.95 g

Sources & evidence

ORD record
ord-c1fcd2e93623467492a9977527ef8353
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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