Dichloromethane → Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-

HRID 1819540Notes

Reaction equation

HRID 1819540 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ClCCl>CN(C)C=O>[CH2:20]([O:8][C:7]1[C:9]([O:10][CH3:11])=[CH:12][C:2]([CH:1]=[O:13])=[CH:3][C:4]=1[O:5][CH3:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 3014502Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-Yield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of syringaldehyde (25.19 g, 138 mmol) and potassium carbonate (38.14 g, 276 mmol, 2 equ) in N,N-dimethyl formamide (500 ml) was added benzyl bromide (20 ml, 168 mmol, 1.2 equ). The reaction was stirred for 25 hours, then poured into dichloromethane. The organic solvent was washed with water (5×) then dried (MgSO4) and concentrated in vacuo to give a pink oil. This was recrystallised from hexane to give 31 (32.9 g, 87 %).

Workup

  1. washThe organic solvent was washed with water (5×)
  2. dry with materialthen dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a pink oil
  5. customThis was recrystallised from hexane

Sources & evidence

ORD record
ord-47143e19c866463cba9a8b562c650494
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

Loading…