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

HRID 621716

Reaction equation

HRID 621716 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.[C:11]([O:14][CH2:15][CH2:16][O:17]C)(=O)C.Cl>C1C=CC=CC=1.O>[CH3:11][O:14][CH2:15][C:16]([CH:6]1[CH2:5][CH:4]([CH3:3])[CH2:9][CH2:8][C:7]1=[O:10])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8054Ethylene glycol monomethyl ether acetateHCID 115254-MethylcyclohexanoneHCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

2.5 g of 60% sodium hydride was suspended in 50 ml of benzene and a mixture of 5.6 g of 4methylcyclohexanone and 5.4 g of methoxyethyl acetate was added dropwise thereto under cooling. After stirring at room temperature for two hours, 20 ml of water was added and the pH value of the reaction mixture was adjusted to 3 with concentrated hydrochloric acid. After removing the benzene phase the aqueous phase was extracted with ether. The benzene solution and the ether solution were combined, washed with water, dried and concentrated to give 7.4 g of crude 2-methoxyacetyl4-methylcyclohexanone. This crude product was subjected to the subsequent step.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling
  3. customAfter removing the benzene phase the aqueous phase
  4. extractionwas extracted with ether
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d6452be3aa04ad5abfcb8b1671e640f
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Linked notes

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