Hydrochloric Acid → 2-(2-Methoxyacetyl)-4-methylcyclohexan-1-one

HRID 231224

Reaction equation

HRID 231224 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.[CH3:11][O:12][CH2:13][C:14](OCC)=[O:15].Cl>C1C=CC=CC=1.O>[CH3:11][O:12][CH2:13][C:14]([CH:6]1[CH2:5][CH:4]([CH3:3])[CH2:9][CH2:8][C:7]1=[O:10])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115254-MethylcyclohexanoneHCID 24758Sodium hydrideHCID 77544Ethyl 2-methoxyacetate

Product 1

HCID 200349082-(2-Methoxyacetyl)-4-methylcyclohexan-1-oneYield 87.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

In 50 ml of benzene was suspended 2.5 g of 60% sodium hydride. While cooling the suspension, a mixture of 5.6 g of 4-methylcyclohexanone and 5.4 g of ethyl methoxyacetate was dropwise added thereto. After stirring at room temperature for 2 hours, 20 ml of water was added thereto and the pH was rendered 3 with concentrated hyrochloric acid. The benzene phase was separated and the aqueous phase was extracted with ether. The benzene solution and the ether solution were combined with each other followed by washing with a sodium chloride aqueous solution. After drying, the mixture was concentrated to give 7.4 g of crude 2-methoxyacetyl-4-methylcyclohexanone. The crude product was used at the following step. (2) 4-Cyano-2,3,5,6,7,8-hexahydro-1-methoxymethyl-7-methyl-3-oxoisoquinoline

Workup

  1. temperatureWhile cooling the suspension
  2. additionwas dropwise added
  3. customThe benzene phase was separated
  4. extractionthe aqueous phase was extracted with ether
  5. washby washing with a sodium chloride aqueous solution
  6. customAfter drying
  7. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-7d7e4b78548b4ce6aea6dafc1effcb5b
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Linked notes

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