Reaction SMILES: [CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:165]=[C:166]([O:187][CH2:188][CH2:189][CH2:190][CH2:191][CH2:192][CH2:193][CH2:194][CH2:195][CH2:196][CH2:197][CH2:198][CH2:199][CH2:200][CH2:201][CH2:202][CH2:203][CH2:204][CH3:205])[C:167]=1[O:168][CH2:169][CH2:170][CH2:171][CH2:172][CH2:173][CH2:174][CH2:175][CH2:176][CH2:177][CH2:178][CH2:179][CH2:180][CH2:181][CH2:182][CH2:183][CH2:184][CH2:185][CH3:186])[CH2:23][O:24][C:25]1[CH:26]=[C:27]([CH:32]=[C:33]([O:100][CH2:101][C:102]2[CH:107]=[C:106]([O:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH2:123][CH2:124][CH2:125][CH3:126])[C:105]([O:127][CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][CH2:144][CH3:145])=[C:104]([O:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154][CH2:155][CH2:156][CH2:157][CH2:158][CH2:159][CH2:160][CH2:161][CH2:162][CH2:163][CH3:164])[CH:103]=2)[C:34]=1[O:35][CH2:36][C:37]1[CH:42]=[C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:40]([O:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])=[C:39]([O:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH3:99])[CH:38]=1)[C:28](OC)=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>COC1CCCC1>[CH2:188]([O:187][C:166]1[CH:165]=[C:22]([CH:21]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:167]=1[O:168][CH2:169][CH2:170][CH2:171][CH2:172][CH2:173][CH2:174][CH2:175][CH2:176][CH2:177][CH2:178][CH2:179][CH2:180][CH2:181][CH2:182][CH2:183][CH2:184][CH2:185][CH3:186])[CH2:23][O:24][C:25]1[CH:26]=[C:27]([CH:32]=[C:33]([O:100][CH2:101][C:102]2[CH:103]=[C:104]([O:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154][CH2:155][CH2:156][CH2:157][CH2:158][CH2:159][CH2:160][CH2:161][CH2:162][CH2:163][CH3:164])[C:105]([O:127][CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][CH2:144][CH3:145])=[C:106]([O:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH2:123][CH2:124][CH2:125][CH3:126])[CH:107]=2)[C:34]=1[O:35][CH2:36][C:37]1[CH:38]=[C:39]([O:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH3:99])[C:40]([O:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])=[C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH:42]=1)[CH2:28][OH:29])[CH2:189][CH2:190][CH2:191][CH2:192][CH2:193][CH2:194][CH2:195][CH2:196][CH2:197][CH2:198][CH2:199][CH2:200][CH2:201][CH2:202][CH2:203][CH2:204][CH3:205]
Reactant: CCCCCCCCCCCCCCCCCCOc1cc(COc2cc(C(=O)OC)cc(OCc3cc(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c3)c2OCc2cc(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c2)cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
Agent: Cl
Agent: [Al+3]
Agent: [H-]
Solvent: COC1CCCC1
Product: CCCCCCCCCCCCCCCCCCOc1cc(COc2cc(CO)cc(OCc3cc(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c3)c2OCc2cc(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c(OCCCCCCCCCCCCCCCCCC)c2)cc(OCCCCCCCCCCCCCCCCCC)c1OCCCCCCCCCCCCCCCCCC
Temperature: 25 °C
Reaction time: 2 h
Yield: 94.5 %

Procedure:
Methyl {3,4,5-tris[3,4,5-tris(octadecyloxy)benzyloxy]}benzoate (1.01 g, 350 μmol) was dissolved in dehydrating cyclopentyl methyl ether (20 mL) and, under ice-cooling, lithium aluminum hydride (31.8 mg, 840 μmol) was added, and the mixture was stirred at room temperature for 2 hr. After completion of the reaction, 0.1 mol/L aqueous hydrochloric acid was added dropwise to decompose unreacted lithium aluminum hydride and the mixture was washed with 1.0 mol/L aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration and dried under reduced pressure to give the title compound (940 mg, 94.6%) as a white solid.