5-Benzyloxy-2-hydroxymethylphenol → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 643947Notes

Reaction equation

HRID 643947 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16][OH:17])=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.CO.O=[Mn]=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]=[O:17])=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 251384215-Benzyloxy-2-hydroxymethylphenol

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-benzyloxy-2-hydroxymethylphenol (2.39 g, 10.4 mmol) in CH2Cl2 (52 mL) and MeOH (5 mL) is added MnO2 (9.05 g, 104 mmol). The suspension is stirred at ambient temperature overnight. The mixture is filtered and the solvent removed under reduced pressure. The crude material is purified by flash chromatography using CH2Cl2 to afford 4-benzyloxy-2-hydroxybenzaldehyde as a pale yellow solid: 1H NMR (CDCl3) δ 11.45 (s, 1H), 9.70 (s, 1H), 7.43-7.39 (m, 6H), 6.59 (dd, J=2.28 Hz), 6.50 (d, J=2.27 Hz, 1H), 5.10 (s, 2H); (M+H)+=229.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent removed under reduced pressure
  3. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-ce4f28cd47be4512b09c5d10aaac9ddd
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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