Methanol → HCID 20373928, compound

HRID 1834667Notes

Reaction equation

HRID 1834667 reaction equation
[CH3:1][CH:2]1[CH:7]([CH2:8][CH3:9])[C:6](=[O:10])[CH2:5][CH2:4][CH:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].CO.[BH4-].[Na+]>C(O)(=O)C>[CH3:1][CH:2]1[CH:7]([CH2:8][CH3:9])[CH:6]([OH:10])[CH2:5][CH2:4][CH:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 20373931HCID 20373931, compound

Product 1

HCID 20373928HCID 20373928, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 22.5 g. of ethyl 2-methyl-3-ethyl-4-ketocyclohexanecarboxylate (all-cis form, m.p. 28°-32°) in 450 ml. of methanol is stirred and maintained at a temperature of 5°-7° C. while a total of 11.0 g. of sodium borohydride is added over a period of 40 minutes. The reaction mixture is stirred at 5° C. for an additional one hour after which a total of 40 ml. of acetic acid is added cautiously to neutralize the base. The methanol solution is evaporated under vacuum to a pasty residue which is shaken with ether and water. The ether phase is washed with aqueous sodium bicarbonate and is dried and evaporated to yield a colorless oil. Upon distillation of the oil, 21.5 g. of ethyl 2-methyl-3-ethyl-4-hydroxycyclohexanecarboxylate is obtained as a mobile oil having a boiling point of 88°-91° at 0.001 mm.

Workup

  1. temperaturemaintained at a temperature of 5°-7° C. while a total of 11.0 g
  2. customThe methanol solution is evaporated under vacuum to a pasty residue which
  3. stirringis shaken with ether and water
  4. washThe ether phase is washed with aqueous sodium bicarbonate
  5. customis dried
  6. customevaporated
  7. customto yield a colorless oil
  8. distillationUpon distillation of the oil, 21.5 g

Sources & evidence

ORD record
ord-e63a2a78f8324ced84d9afbe1a93cd49
Source dataset
uspto-grants-1978_01
Patent number
US04070541

Reaction notes

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