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

HRID 1809808Notes

Reaction equation

HRID 1809808 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-536b0e60212848bb92409862afa0bbd4
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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