Hydrochloric Acid → [3-(4-Methoxy-butyl)-phenyl]-methanol

HRID 1809817Notes

Reaction equation

HRID 1809817 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].CO.[BH4-].[Na+].Cl>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 860534433-(4-Methoxy-butyl)-benzaldehyde

Product 1

HCID 67544100[3-(4-Methoxy-butyl)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title D compound, 3-(4-methoxy-butyl)-benzaldehyde (0.1 g, 0.52 mmol) and MeOH (0.063 mL, 1.56 mmol) in 2 mL of THF is added portion wise sodium borohydride (20 mg, 0.52 mmol). The reaction mixture is stirred for 1 hour at room and poured into aqueous 1M HCl. The aqueous layer is extracted twice with ethyl acetate and 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 3/1) to afford the title compound as a colorless oil: TLC, Rf (hexane/AcOEt 2/1)=0.34. MS 212.1 [M+18].

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
  4. customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 3/1)

Sources & evidence

ORD record
ord-818711c7de9c4655951270d0b12ae5d6
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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