Hydrochloric Acid → methyl 4-acetylcyclohexanecarboxylate

HRID 129281Notes

Reaction equation

HRID 129281 reaction equation
[C:1]([C:4]1(C(OC)=O)[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.O>C(O)C>[C:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22421025HCID 22421025, compound

Product 1

HCID 22421109methyl 4-acetylcyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethyl 1-acetylcyclohexane-1,4-dicarboxylate (23.3 g) was added to a solution of concentrated hydrochloric acid (253 ml) in ethanol (126 ml). After refluxing for 10 hours the reaction mixture was poured into water and then extracted with dichloromethane. The organic phase was then washed with saturate sodium bicarbonate solution and brine. After drying over anhydrous magnesium sulphate the solvent was removed under reduced pressure to give methyl 4-acetylcyclohexanecarboxylate as a colourless oil. This was purified by distillation (b.pt 138°-145° C. at 14 mmHg).

Workup

  1. temperatureAfter refluxing for 10 hours the reaction mixture
  2. extractionextracted with dichloromethane
  3. washThe organic phase was then washed with saturate sodium bicarbonate solution and brine
  4. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-dff292b964a749679136b2ad8c73d0b2
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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