Salicylaldehyde → HCID 14676386, compound

HRID 1905856Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][C:11]([CH3:20])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]I>>[CH3:10][C:11]([CH3:20])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

Reactant 2

HCID 6998Salicylaldehyde

HCID 14676385HCID 14676385, compound

Product 1

HCID 14676386HCID 14676386, compound

Procedure

2-Hydroxybenzaldehyde was condensed with 2,2-dimethyl-1-iodo octane to yield 2-(2,2-dimethyl octyloxy)benzaldehyde which was reduced to 2-(2,2-dimethyl, octyloxy)benzyl alcohol and then converted to [[2-(2,2-dimethyloctyloxy)phenyl]methyl]triphenylphosphonium bromide as in Example 1. Condensation of this phosphonium bromide with 7-formyl-3-methyl-2,4,6-octatrienoic acid ethyl ester as described in Example 3 followed by hydrolysis, as in Example 5, gave the (All-E)-3,7-Dimethyl-9-[2-[(2,2-dimethyl-octyl)oxy]phenyl]-2,4,5,8-non-atetraenoic acid mp 113°-117° (from dichloromethane/hexane mixture).

Sources & evidence

ORD record: ord-7ba9b18007ed4493af2e89906a85205e
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04648996

Reaction notes

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