5-Chloro-2-(hydroxymethyl)phenol → 4-Chloro-2-hydroxybenzaldehyde

HRID 1241467Notes

Reaction equation

HRID 1241467 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1>ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:9]=[O:10])=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 1

HCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 5201014-Chloro-2-hydroxybenzaldehydeYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,3-Dichloro-5,6-dicyano-1-4-benzoquinone (DDQ, 9.92 g, 43.7 mmol) was added to a solution of 5-chloro-2-hydroxymethylphenol in dichloromethane (65 mL) and tetrahydrofuran (15 mL). The reaction mixture was stirred at room temperature for 4 h. Then, the solvent was evaporated under vacuum and the crude was purified by chromatography on silica to afford the title compound (72%):

Workup

  1. customThen, the solvent was evaporated under vacuum
  2. customthe crude was purified by chromatography on silica

Sources & evidence

ORD record
ord-cb773260effe42a080b6a0e36474d701
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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