Acetic Anhydride → (4-Phenylcyclohexyl) acetate

HRID 1737930Notes

Reaction equation

HRID 1737930 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15](OC(C)=O)=[O:16]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:15]([O:13][CH:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)(=[O:16])[CH3:14]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 794974-Phenylcyclohexanol

Product 1

HCID 226557(4-Phenylcyclohexyl) acetateYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of 20.3 g (0.115 mol) of 4-phenylcyclohexanol, 14.2 ml (O.1S mol) of acetanhydride and 29 ml of triethylamine are added, with stirring and at ambient temperature, 2.3 g (0.02 mol) of 4-dimethylaminopyridine, a clear solution being produced in an exothermic reaction. This is heated to 80° C. for 3 hours and the reaction mixture is then poured into ice water. The crystalline product precipitated is suction filtered, dissolved in ether, washed with sodium bicarbonate solution, dried and evaporated down in vacuo. 23 g (92% of theory) of O-acetyl-4-phenylcyclohexanol are obtained. The product is obtained initially as an oil but crystallises when left to stand. Melting point: 43-45° C.

Workup

  1. additionare added
  2. temperatureThis is heated to 80° C. for 3 hours
  3. customThe crystalline product precipitated
  4. filtrationfiltered
  5. dissolutiondissolved in ether
  6. washwashed with sodium bicarbonate solution
  7. customdried
  8. customevaporated down in vacuo

Sources & evidence

ORD record
ord-40645d504a3548508b2f0fa33711be8b
Source dataset
uspto-grants-1999_10
Patent number
US05962507

Reaction notes

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