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

反応式

[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]

参加物

反応物 4

HCID 87683,4-Dihydroxybenzaldehyde

HCID 77547Ethyl 3,4-Dihydroxybenzoate

HCID 58403839-Octadecene, 1-bromo-, (9Z)-2 回

HCID 161030163,4-Dioleyloxybenzaldehyde

生成物 1

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

実験手順

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.