Benzyl Bromide → 3-(Benzyloxy)-2-hydroxybenzaldehyde

HRID 983785Notes

Reaction equation

HRID 983785 reaction equation
[H][H].[OH:3][C:4]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)S(=O)=O.O>[CH2:15]([O:12][C:11]1[C:4]([OH:3])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 905792,3-DihydroxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 112876163-(Benzyloxy)-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 178486088HCID 178486088, compoundSolvent2×

Procedure

Scheme V depicts a method of preparing aldehyde 13. For example, an aldehyde of formula 11 wherein R3, R4 and R5 are hydrogen, i.e., 2,3-dihydroxybenzaldehyde (0.6 g, 4.3 mmol) was added to dimethyl sulfonamide (DMSO) (10 ml) containing sodium hydride (0.25 g, 10.4 mmol). After one hour a solution of benzyl bromide (0.52 ml, 4.3 mmol) in DMSO (5 ml) is added. Stirring the mixture is continued for 24 h, after which time the mixture is poured into water and extracted with chloroform (2×). The aqueous solution then was acidified with 6N hydrochloric acid to adjust the pH from 2 to about 4 and extracted with chloroform (3×). The latter organic layers were washed with 1N hydrochloric acid and filtered over silica gel to give 3-benzyloxy-2-hydroxy benzaldehyde.

Workup

  1. extractionextracted with chloroform (2×)
  2. extractionextracted with chloroform (3×)
  3. washThe latter organic layers were washed with 1N hydrochloric acid
  4. filtrationfiltered over silica gel

Sources & evidence

ORD record
ord-274e44a98125408ca63fea6c7e95f8e8
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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