Hydrochloric Acid → (4-(Propan-2-yloxy)phenyl)methanol

HRID 1678591Notes

Reaction equation

HRID 1678591 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CO>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][OH:10])=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2500774-IsopropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 250081(4-(Propan-2-yloxy)phenyl)methanolYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

With ice cooling, to a solution of 4-isopropoxybenzaldehyde (0.93 g, 5.6 mmol) in methanol (20 mL) was added a solution of sodium tetrahydroborate (0.32 g, 11 mmol) in methanol (10 mL), and the mixture was stirred at room temperature for 4 hours. The mixture was acidified by adding 2 N hydrochloric acid to the reaction solution, and extracted with diethyl ether. The extract was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (0.76 g, yield 81%) as an oily matter.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-8da31b0a41b94f90b906d761af104789
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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