4-Hydroxybenzaldehyde → p-Nonyloxybenzaldehyde

HRID 1484062Notes

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][CH2:17][CH2:18][CH3:19]>>[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][CH2:17][CH2:18][CH3:19]

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 127421-Bromononane

Product 1

HCID 142697p-NonyloxybenzaldehydeYield 79.3%

Procedure

General procedure K was used to convert 4-hydroxybenzaldehyde (8.2 mmols) and 1-bromononane (12.3 mmols) to 6.5 mmols (79%) of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 9.88 (s, 1H), 7.83 (d, J=8.9 Hz, 2H), 6.99 (d, J=8.7 Hz, 2H), 4.04 (t, J=6.6 Hz, 2H), 1.76-1.85 (m, 2H), 1.14-1.53 (m, 12H), 0.88 (t, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 164.40, 132.11, 114.86, 68.55, 31.98, 29.47, 29.37, 29.18, 28.90, 28.31, 26.08, 22.79, 14.23.

Sources & evidence

ORD record: ord-c2191b3aa8e5473faedf566cf3ddab14
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421177B2

Reaction notes

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