Hydrochloric Acid → HCID 178447882, compound

HRID 1589739Notes

Reaction equation

HRID 1589739 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Cl>C1(C)C=CC=CC=1>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178447883HCID 178447883, compound

Product 1

HCID 178447882HCID 178447882, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

100 cm3 of toluene was added to 170 cm3 (0.6 mol) of 70% toluene solution of NaAlH2 (OC2H4OCH3)2. 133 g (0.50 mol) of 4-(trans-4'-propylcyclohexyl) benzoic acid chloride was added drop-wise to the solution while stirring at a rate to moderately reflux the toluene solution and the mixture was stirred over a warm water bath at a temperature of 88°-90° C. for 5 hours. The solution was cooled to room temperature and 500 cm3 of concentrated hydrochloric acid diluted by twice its volume was added drop-wise. The toluene layer was separated out and the aqueous layer was extracted three times with 100 cm3 of toluene. The toluene layers were combined and washed with 10% hydrochloric acid and water. The toluene was distilled off under reduced pressure and the residue was distilled under reduced pressure (150° C./2.5 mmHg) to yield 114 g (0.49 mol) of 4-(trans-4'-propylcyclohexyl) benzyl alcohol.

Workup

  1. stirringthe mixture was stirred over a warm water bath at a temperature of 88°-90° C. for 5 hours
  2. additionwas added drop-wise
  3. customThe toluene layer was separated out
  4. extractionthe aqueous layer was extracted three times with 100 cm3 of toluene
  5. washwashed with 10% hydrochloric acid and water
  6. distillationThe toluene was distilled off under reduced pressure
  7. distillationthe residue was distilled under reduced pressure (150° C./2.5 mmHg)

Sources & evidence

ORD record
ord-9d32daef0eeb47e2a44854756c908f0b
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

Loading…