Hydrochloric Acid → methyl 4-acetylcyclohexanecarboxylate

HRID 1441036Notes

Reaction equation

HRID 1441036 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>CO>[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 887MethanolSolvent

Procedure

Dimethyl 1-acetylcyclohexane-1,4-dicarboxylate (23.3 g.) was added to a solution of concentrated hydrochloric acid (253 ml.) in methanol (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 saturated 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.p. 138°-145°/14 mmHg). Nuclear Magnetic Resonance spectrum (NMR) was as follows: 3.60, 3H, s; 2.6-1.2, 13H, m.

Workup

  1. temperatureAfter refluxing for 10 hours the reaction mixture
  2. extractionextracted with dichloromethane
  3. washThe organic phase was then washed with saturated 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-1f88a14f65a64f92aa2c9b9fa7ccc1c1
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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