Water → 2,6-Dihydroxybenzaldehyde

HRID 660620Notes

Reaction equation

HRID 660620 reaction equation
C([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]CC2C=CC=CC=2)[C:10]=1[CH:11]=[O:12])C1C=CC=CC=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:10]=1[CH:11]=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 117268902,6-Bis-benzyloxybenzaldehyde

Product 1

HCID 102858012,6-Dihydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-bis-benzyloxybenzaldehyde (1.9 g, 6 mmol) in methylene chloride (15 mL) is added BBr3 (18 mL, 18 mmol, 1M in methylene chloride) and the mixture is stirred at RT for 18 h. Water is added to the mixture and the methylene chloride is removed under reduced pressure. The aqueous is extracted with EtOAc and the organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (5:1) as eluent to give the title compound as a yellow solid.

Workup

  1. customthe methylene chloride is removed under reduced pressure
  2. extractionThe aqueous is extracted with EtOAc
  3. washthe organic phase is washed with water and brine
  4. dry with materialthen is dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-3cf32c6e307749189fca42ffb0a00e50
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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