Benzyl Bromide → 4-Benzyloxy-3-hydroxybenzaldehyde

HRID 1879553Notes

Reaction equation

HRID 1879553 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 5613694-Benzyloxy-3-hydroxybenzaldehydeYield 50.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,4-dihydroxybenzaldehyde (1.38 g, 10 mmol), benzyl bromide (1.71 g, 10 mmol), and K2CO3 (1.24 g, 9 mmol) in 20 mL acetone was stirred at rt for 15 h under Ar atmosphere. Solid was filtered off and the filtrated was diluted with EtOAc (100 mL) and washed with NaH2PO4 (sat. 100 mL), and dried over MgSO4 and concentrated. The residue was chromatographed (hexane/EtOAc) to afford 4-(benzyloxy)-3-hydroxybenzaldehyde as a white solid (1.15 g, 50%). 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.44-7.40 (m, 6H), 7.04 (d, J=8.0 Hz, 1H), 5.80 (s, 1H), 5.21 (s, 2H); MS (ESI) m/z 229 (M+H+).

Workup

  1. filtrationSolid was filtered off
  2. additionthe filtrated was diluted with EtOAc (100 mL)
  3. washwashed with NaH2PO4 (sat. 100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed (hexane/EtOAc)

Sources & evidence

ORD record
ord-b7eb96e3a2474ed2a818218ec209ba5f
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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