Sodium borohydride → HCID 17824041, compound

HRID 1169464Notes

Reaction equation

HRID 1169464 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[CH:7]=[O:8])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[CH2:7][OH:8])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 17609227HCID 17609227, compound

Product 1

HCID 17824041HCID 17824041, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 3-ethoxy-4-(2-propoxyethoxy)benzaldehyde (7.34 g) in methanol (30 ml) was added at 0° C. sodium borohydride (1.10 g), and the resulting mixture was stirred for one hour. After concentration under reduced pressure, 1 N hydrochloric acid was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. The resulting organic layer was concentrated under reduced pressure to obtain 3-ethoxy-4-(2-propoxyethoxy)benzyl alcohol (7.35 g) as a colorless oily substance.

Workup

  1. concentrationAfter concentration under reduced pressure, 1 N hydrochloric acid
  2. additionwas added to the reaction mixture, which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialwas dried with magnesium sulfate
  6. concentrationThe resulting organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7b0b7a6c36546ca858a326bbaa6d9a3
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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