Potassium Carbonate → 2-Benzyloxy-5-methoxy-benzaldehyde

HRID 1096678Notes

Reaction equation

HRID 1096678 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].F[C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:16]1[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 8784742-Benzyloxy-5-methoxy-benzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-hydroxy-5-methoxybenzaldehyde (0.152 g, 1.0 mmol) in dry MeCN (50 mL) was added 4-fluorobenzyl bromide (0.145 mg, 1.0 mmol), and anhydrous K2CO3 (0.27 g, 2.0 mmol). The mixture was refluxed under stirring for 4 h, and then evaporated in vacuo. Water (100 mL) was added and the mixture was extracted with EtOAc. The separated organic layer was dried with MgSO4, and then evaporated in vacuum. Finally, the residue was eluted through a silica gel column with n-hexane/EtOAc (4:1) to give white compound I (0.21 g, 88%).

Workup

  1. temperatureThe mixture was refluxed
  2. customevaporated in vacuo
  3. additionWater (100 mL) was added
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe separated organic layer was dried with MgSO4
  6. customevaporated in vacuum
  7. washFinally, the residue was eluted through a silica gel column with n-hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-bb68b901dcb44636822a38820b58eafb
Source dataset
uspto-grants-2012_03
Patent number
US08138360B2

Reaction notes

Loading…