Benzyl Bromide → HCID 15947956, compound

HRID 1881191Notes

Reaction equation

HRID 1881191 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N12CCCN=C1CCCCC2.[OH-].[Na+]>CN(C)C=O>[CH2:13]([O:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 111945542,4-Dihydroxy-5-methoxybenzaldehyde

Product 1

HCID 15947956HCID 15947956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dihydroxy-5-methoxybenzaldehyde (6.0 g), benzyl bromide (9.7 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (8.6 g) in N,N-dimethylformamide (30 ml) were heated at 100° C. under nitrogen for 5 hours. After cooling to room temperature, 1 N NaOH was added and the mixture washed with ethyl acetate. The water phase was acidified with HCl and the precipitate was filtered.

Workup

  1. washthe mixture washed with ethyl acetate
  2. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-a4e8737928624adeb493592c1b8c24a4
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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