3-Hydroxybenzaldehyde → 3-(5-Benzyloxypentoxy)-benzaldehyde

HRID 875593Notes

Reaction equation

HRID 875593 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][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O>>[CH2:21]([O:20][CH2:19][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:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 446271175-(benzyloxy)pentyl Methanesulfonate

Product 1

HCID 866376213-(5-Benzyloxypentoxy)-benzaldehyde

Procedure

Alkylation reaction of 3-hydroxybenzaldehyde with 5-(benzyloxy)pentyl methanesulfonate gave 3-(5-(benzyloxy)pentyloxy)benzaldehyde as a clear oil. Yield (1.3 g, 66%): 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 7.42-7.46 (m, 2H), 7.25-7.39 (m, 6H), 7.15-7.18 (m, 1H), 4.51 (s, 2H), 4.02 (t, J=6.4 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 1.82-1.89 (m, 2H), 1.68-1.76 (m, 2H), 1.54-1.62 (m, 2H).

Sources & evidence

ORD record
ord-fee5a8328e6342d8bebe3c199104de22
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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