Benzyl Bromide → 4-Benzyloxy-3-hydroxybenzaldehyde

HRID 987866Notes

Reaction equation

HRID 987866 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[I-].[K+].CC(C)=O>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

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

Product 1

HCID 5613694-Benzyloxy-3-hydroxybenzaldehydeYield 39.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 5.52 g (40 mmol) of 3,4-dihydroxybenzaldehyde, 6.09 g (44 mmol) of potassium carbonate, 70 mg of potassium iodide, 110 ml of acetone and 6.84 g (40 mmol) of benzyl bromide was refluxed for 15 hours. Thereafter, the mixture was cooled, the reaction suspension was filtered and the filtrate was evaporated down. Chromatography of the residue over silica gel using 9:1 toluene/ethyl acetate gave 3.6 g of 4-benzyloxy-3-hydroxybenzaldehyde.

Workup

  1. temperaturewas refluxed for 15 hours
  2. temperatureThereafter, the mixture was cooled
  3. filtrationthe reaction suspension was filtered
  4. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-4bcdaa72f12c4f0495dec7c493dd127e
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

Loading…