Hydrochloric Acid → (4-Cyclopropylphenyl)methanol

HRID 1615050Notes

Reaction equation

HRID 1615050 reaction equation
[BH4-].[Na+].[CH:3]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.Cl>C(O)C>[CH:3]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:12][CH:13]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 115064744-Cyclopropylbenzaldehyde2×

Product 1

HCID 22135711(4-Cyclopropylphenyl)methanolYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of NaBH4 (15 g) in ethanol (180 mL) was added the crude 4-cyclopropylbenzaldehyde prepared in (1) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added 6 N hydrochloric acid (90 mL) at 0° C. The reaction mixture was stirred for 30 min and then concentrated in vacuo. Water was added to the residue and the mixture was extracted with toluene. The solvent was removed under reduced pressure. The resulting residue was distilled under reduced pressure to give the title compound (60 g, 79%).

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. concentrationconcentrated in vacuo
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with toluene
  5. customThe solvent was removed under reduced pressure
  6. distillationThe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-40415c735f7d4412ab069d75b2cf391f
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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