Water → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

HRID 2354969Notes

Reaction equation

HRID 2354969 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16].[BH4-].[Na+].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehyde

Product 1

HCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title A compound, 4-methoxy-3-(3-methoxy-propoxy)-benzaldehyde (2.02 g, 8.9 mmol) in 60 mL of THF is added portion wise sodium borohydride (0.74 g, 18.73 mmol) at 0° C. The reaction mixture is stirred for 6 hours at room temperature. 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 to afford the title compound as a colorless oil: TLC, Rf (hexane/AcOEt 1/1)=0.34.

Workup

  1. extractionthe aqueous layer is extracted twice with ethyl acetate
  2. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbfd4239b9db4a3388af74214d9cd7fb
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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