Hydrochloric Acid → 2-Acetyl-4-methoxycyclohexanone

HRID 621710

Reaction equation

HRID 621710 reaction equation
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.Cl>O.CO.C1C=CC=CC=1>[C:3]([CH:15]1[CH2:16][CH:11]([O:10][CH3:9])[CH2:12][CH2:13][C:14]1=[O:17])(=[O:5])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 5350284-Methoxycyclohexanone

Product 1

HCID 136327242-Acetyl-4-methoxycyclohexanone

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.12 g of 60% sodium hydride was added to 2.5 g of ethyl acetate and 1.78 g of a benzene solution of 4-methoxycyclohexanone was added thereto. After reacting at 40° C. for three hours, methanol was added to thereby decompose excessive sodium hydride and the reaction mixture was poured into water, neutralized with hydrochloric acid and extracted with ether to give 1.02 g of 2-acetyl4-methoxycyclohexanone. NMRδTMSCCl4 : 2.06 (3H, s). 1.7-2.5 (8H, s), 3.28 (3H , s), 3.4 (1H, m) and 15.9 (1H, s).

Workup

  1. additionwas added
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-4cb7820e2c0d4756ac91ec0260e9fb9c
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Linked notes

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