3-Hydroxybenzaldehyde → 3-(2-Hydroxypentyloxy)benzaldehyde

HRID 875589Notes

Reaction equation

HRID 875589 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[O:10]1[CH:12]([CH2:13][CH2:14][CH3:15])[CH2:11]1>>[OH:10][CH:12]([CH2:13][CH2:14][CH3:15])[CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

3

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 13853Oxirane, 2-propyl-

Product 1

HCID 866376233-(2-Hydroxypentyloxy)benzaldehyde

Procedure

Alkylation reaction of 3-hydroxybenzaldehyde with 1,2-epoxypentane gave 3-(2-hydroxypentyloxy)benzaldehyde as a clear oil. Yield (0.6 g, 24%): 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 7.42-7.49 (m, 2H), 7.40 (s, 1H), 7.21 (d, J=7.2 Hz, 1H), 4.04 (d, J=7.2 Hz, 2H), 3.87-3.93 (m, 1H), 2.28 (d, J=3.6 Hz, 1H), 1.42-1.62 (m, 4H), 0.98 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-4ba6435ba97140c6bcd9fb2443031117
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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