3,4-Dihydroxybenzaldehyde → Ethyl 3,4-di(oleyloxy)benzoate

HRID 604757Notes

Reaction equation

HRID 604757 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:23]=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:47][C:48]1C=C(C=C[C:55]=1O)C=O.C(Br)CCCCCCC/C=C\CCCCCCCC.OC1C=C(C=CC=1O)C(OCC)=O>>[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:23]([O:47][CH2:48][CH3:55])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 87683,4-DihydroxybenzaldehydeHCID 77547Ethyl 3,4-DihydroxybenzoateHCID 58403839-Octadecene, 1-bromo-, (9Z)-2×HCID 161030163,4-Dioleyloxybenzaldehyde

Product 1

HCID 16102993Ethyl 3,4-di(oleyloxy)benzoate

Procedure

The first step was the synthesis of 3,4-di(oleyloxy)benzaldehyde 8a by the O-alkylation of 3,4-dihydroxy benzaldehyde 7a with oleyl bromide (Scheme 1 as shown in FIG. 3). Similarly, the bis-O-alkylation of ethyl 3,4-dihydroxybenzoate 7b with oleyl bromide was used to form ethyl 3,4-di(oleyloxy)benzoate 8b using the method of Safinya et al.,23,24 Subsequent cleavage of 8b with KOH was carried out to give the acid 8c (Scheme 1) followed by treatment with oxalyl chloride to give the desired acid chloride 8d.

Sources & evidence

ORD record
ord-eadeb342c20b43c2bb2d0423e9c73e4b
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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