Hydrochloric Acid → HCID 178445623, compound

HRID 1707535Notes

Reaction equation

HRID 1707535 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12](O)=[O:13])[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][CH2:12][OH:13])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178445626HCID 178445626, compound

Product 1

HCID 178445623HCID 178445623, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
90 °C

Procedure

37 g (0.19 mol) of trans-4-butylcyclohexyl acetic acid was dispersed in 190 cm) of anhydrous toluene, 160 cm3 (0.57 mol) of 70% of NaAlH2 (OC2H4OCH3)2 in toluene was added dropwise while stirring 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, 40 cm3 of water and 500 cm3 of 15% HCl were added dropwise while stirring, the oily layer was taken off, and the water layer was extracted with toluene, combined with the oily layer and washed with 10% HCl and water. The toluene was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 103° C./3 mmHg) to obtain 31 g (0.17 mol) of 2-(trans-4'-butylcyclohexyl)ethanol.

Workup

  1. additionwas added dropwise
  2. temperaturerefluxed quietly
  3. temperatureThe reactant was cooled to room temperature
  4. stirringwhile stirring
  5. extractionthe water layer was extracted with toluene
  6. washwashed with 10% HCl and water
  7. customThe toluene was removed
  8. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 103° C./3 mmHg)

Sources & evidence

ORD record
ord-c1e6c4ca22694117b0f929bab46a130e
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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