Hydrochloric Acid → HCID 178445651, compound

HRID 1707531Notes

Reaction equation

HRID 1707531 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].O.Cl>C1(C)C=CC=CC=1>[CH2:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][OH:12])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178445662HCID 178445662, compound

Product 1

HCID 178445651HCID 178445651, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

55 g (0.30 mol) of trans-4-butylcyclohexane carboxylic acid was dispersed in 200 cm3 of toluene, and while stirring at room temperature, 250 cm3 (0.90 mol) of a 70% NaAlH2 (OC2H4OCH3)2 in toluene was added dropwise at a rate where the toluene refluxed quietly, after which it was stirred for 3 hours on a 90° C. hot water bath. The reactant was cooled to room temperature, cm3 of water and 300 cm3 of 15% HCl were added dropwise while stirring, the oily layer was taken off, the water layer was extracted with toluene and combined with the oily layer, and they were washed with 10% HC1 and water. The toluene was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 100° C./2 mmHg) to obtain 37 g (0.22 mol) of trans-4-butylcyclohexylmethanol.

Workup

  1. temperaturerefluxed quietly
  2. stirringafter which it was stirred for 3 hours on a 90° C. hot water bath
  3. temperatureThe reactant was cooled to room temperature
  4. stirringwhile stirring
  5. extractionthe water layer was extracted with toluene
  6. washwere washed with 10% HC1 and water
  7. customThe toluene was removed
  8. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 100° C./2 mmHg)

Sources & evidence

ORD record
ord-aeaaedde9cd2407fa1a4bac719da60ec
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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