4-Hydroxybenzaldehyde → 4-[(4-methoxybenzyl)oxy]benzaldehyde

HRID 927027Notes

Reaction equation

HRID 927027 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 41542764-[(4-methoxybenzyl)oxy]benzaldehyde

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (10 g, 81.9 mmol) in DMF (200 mL) was added K2CO3 (14.7 g, 106 mmol), tetrabutylammonium iodide (3.06 g, 8.2 mmol) and 4-methoxybenzyl chloride (14.1 g, 90 mmol). The reaction mixture was stirred for 14 h at rt and then poured into ice water. The product 4-(4-methoxy-benzyloxy)-benzaldehyde was isolated by filtration.

Sources & evidence

ORD record
ord-b880ce3399cf4e16a5459f6ab4774ab9
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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