3-(4-Methoxyphenoxy)benzaldehyde → HCID 12799247, compound

HRID 1393346Notes

Reaction equation

HRID 1393346 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[O:14])=[CH:7][CH:6]=1>C(O)C>[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH2:13][OH:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 1235533-(4-Methoxyphenoxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12799247HCID 12799247, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (158 mg, 4.18 mmol) was added to a solution of 3-[(4-methoxy)phenoxy]benzaldehyde (573 mg, 2.51 mmol) in ethanol (10 ml) with stirring under ice cooling, and the mixture was stirred at room temperature for 25 min. The solvent was distilled off from the reaction mixture, and the residue was diluted with ethyl acetate, washed with water and brine in turn and dried. The solvent was distilled off and the residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=20) to give 3-[(4-methoxy)phenoxy]benzyl alcohol (469 mg, 81%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 25 min
  2. distillationThe solvent was distilled off from the reaction mixture
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with water and brine in turn
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=20)

Sources & evidence

ORD record
ord-df63ffe23c5f47d0a9334052215ce2ff
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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