Acetic Anhydride → HCID 13632725, compound

HRID 621714Notes

Reaction equation

HRID 621714 reaction equation
[B].[C:2]1([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1>[C:15]([CH:10]1[CH2:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12][C:11]1=[O:14])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 786054-PhenylcyclohexanoneHCID 517165Ammonium AcetateHCID 5462311Boron

Product 1

HCID 13632725HCID 13632725, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.5 g of boron trifuloride/acetic acid complex was cooled with ice and a benzene solution of 2 g of 4-phenylcyclohexanone and 2.35 g of acetic anhydride was added thereto dropwise. After stirring under ice cooling for 30 min and then at room temperature for four hours, 10 ml of a saturated aqueous solution of ammonium acetate was added thereto and the obtained reaction mixture was stirred at 80° C. for 1.5 hour and purified by extracting with ether to give 1.77 g of 2-acetyl-4phenylcyclohexanone. m.p.: 53-54° C. NMRδTMSDMSO-d6 : 1.90 (3H, m), 2.10 (3H, s), 2.50 (6H, m), 7.26 (5H, s) and 10.58 (1H, s).

Workup

  1. waitat room temperature for four hours
  2. customthe obtained reaction mixture
  3. stirringwas stirred at 80° C. for 1.5 hour
  4. custompurified
  5. extractionby extracting with ether

Sources & evidence

ORD record
ord-8e2eca7f068e4e02a4057628f45588f8
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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