Hydrochloric Acid → Ethyl 2-hydroxycyclohexane-1-carboxylate

HRID 1074099Notes

Reaction equation

HRID 1074099 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl>C(OCC)C>[OH:12][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 303691Ethyl 2-hydroxycyclohexane-1-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.2 g of borane/tert-butylamine complex was added to 200 ml of diethyl ether solution containing 17.0 g (0.10 mol) of ethyl 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 thus separated was dried, concentrated and then distilled under reduced pressure to obtain 13.5 g of ethyl 2-hydroxycyclohexanecarboxylate. Yield: 78.5%. b.p. 68° to 71° C. (0.2 mmHg).

Workup

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

Sources & evidence

ORD record
ord-b32f7d62585c4c11ab707fa6ff6f14dc
Source dataset
uspto-grants-1990_11
Patent number
US04973354

Reaction notes

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