Water → [2-(3-Methoxy-propoxy)-4-methyl-phenyl]-methanol

HRID 2354965Notes

Reaction equation

HRID 2354965 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[BH4-].[Na+].O>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:8]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 860534322-(3-Methoxypropoxy)-4-methylbenzaldehyde

Product 1

HCID 67542816[2-(3-Methoxy-propoxy)-4-methyl-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title B compound, 2-(3-methoxy-propoxy)-4-methyl-benzaldehyde (3.7 g, 17.41 mmol) in 30 mL of methanol is added portion wise sodium borohydride (1.03 g, 26.12 mmol). The reaction mixture is stirred for 30 min at room temperature. Sodium borohydride (1.03 g, 26.12 mmol) is added and the mixture further stirred overnight to complete the reaction. After addition of H2O, the aqueous layer is extracted twice with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 4/1 to 1/2) to afford the title compound as a colorless oil: TLC, Rf (hexane/AcOEt 2/1)=0.2. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 4.88 min.

Workup

  1. stirringthe mixture further stirred overnight
  2. customthe reaction
  3. extractionthe aqueous layer is extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 4/1 to 1/2)

Sources & evidence

ORD record
ord-24797b503bae4fc8a9dae0fbe262852d
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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