Hydrochloric Acid → Ethyl 2-hydroxycyclohexane-1-carboxylate

HRID 1074098Notes

Reaction equation

HRID 1074098 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].Cl.[CH2:13](OCC)C>>[OH:11][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:3]([O:2][CH2:1][CH3:13])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 170489Cyclohexanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 303691Ethyl 2-hydroxycyclohexane-1-carboxylateYield 84.8%

Procedure

3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 15.6 g (0.10 mol) of methyl cyclohexanone-2-carboxylate and stirred overnight at room temperature. An aqueous diluted hydrochloric acid was added thereto to make it weakly acidic, which was then subjected to liquid-liquid separation. The organic layer separated was dried, concentrated and then distilled under reduced pressure to obtain 13.4 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 84.8%. b.p. 60° to 62° C. (0.3 mmHg).

Workup

  1. customwhich was then subjected to liquid-liquid separation
  2. customThe organic layer separated
  3. customwas dried
  4. concentrationconcentrated
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-10d89e5343df4317803f73c6d282bdef
Source dataset
uspto-grants-1990_11
Patent number
US04973354

Reaction notes

Loading…