4-Hydroxybenzaldehyde → Benzaldehyde, 4-(heptyloxy)-

HRID 1484061Notes

Reaction equation

HRID 1484061 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 123691-Bromoheptane

Product 1

HCID 119740Benzaldehyde, 4-(heptyloxy)-Yield 80.5%

Procedure

General procedure K was used to convert 4-hydroxybenzaldehyde (8.2 mmols) and 1-bromoheptane (12.3 mmols) to 6.6 mmols (80%) of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 9.87 (s, 1H), 7.82 (d, J=8.8 Hz, 2H), 6.99 (d, J=8.7 Hz, 2H), 4.03 (t, J=6.5 Hz, 2H), 1.81 (quin., J=6 Hz, 1H), 1.24-1.53 (m, 8H), 0.89 (t, J=6.8 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 191.0, 164.4, 132.13, 129.8, 114.9, 68.6, 31.9, 29.18, 29.1, 26.1, 22.7, 14.2.

Sources & evidence

ORD record
ord-06d1c267a6864cdf8cf8f636f89a1a16
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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