3-Hydroxybenzaldehyde → 3-(4-Benzyloxybutoxy)benzaldehyde

HRID 74420Notes

Reaction equation

HRID 74420 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CS(O[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)=O>>[CH2:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 22033037HCID 22033037, compound

Product 1

HCID 580277083-(4-Benzyloxybutoxy)benzaldehyde

Procedure

Alkylation reaction of 3-hydroxybenzaldehyde (11) with 4-(benzyloxy)butyl methanesulfonate following the method used in Example 149 gave 3-(4-(benzyloxy)butoxy)benzaldehyde (137) as a clear oil. Yield (1.5 g, 80%): 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 7.42-7.46 (m, 2H), 7.33-7.38 (m, 5H), 7.28-7.31 (m, 1H), 7.14-7.18 (m, 1H), 4.53 (s, 2H), 4.04 (t, J=6.4 Hz, 2H), 3.56 (t, J=6.4 Hz, 2H), 1.88-1.98 (m, 2H), 1.80-1.87 (m, 2H).

Sources & evidence

ORD record
ord-dc9234d9b6f24632a716ced0dd8a5211
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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