3-(3-(Hydroxymethyl)phenyl)propan-1-ol → 3-(3-Hydroxypropyl)benzaldehyde

HRID 446388Notes

Reaction equation

HRID 446388 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1>ClCCl.[O-2].[O-2].[Mn+4]>[OH:12][CH2:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 552676803-(3-(Hydroxymethyl)phenyl)propan-1-ol2×

Product 1

HCID 581686063-(3-Hydroxypropyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (2.07 g) was added to a solution of 3-(3-(hydroxymethyl)phenyl)propan-1-ol [Aromatic Intermediate 18, step b] (0.40 g) in dichloromethane (20 mL) and the mixture stirred at ambient temperature for 18 hours. The mixture was filtered through Celite and concentrated in vacuo. The crude product was purified by flash silica chromatography, elution gradient 40%, 50% and 60% ethyl acetate in isohexane. Fractions containing the product were evaporated to dryness to afford the titled compound as a colourless oil. Yield 0.21 g.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by flash silica chromatography, elution gradient 40%, 50% and 60% ethyl acetate in isohexane
  4. additionFractions containing the product
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-f50d2f7653aa47c1b170fc5380ef2f2b
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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