11-[2,3-Difluorobiphenyl-4'-yl]oxyundecyl 2,2-bis(6-benzyloxyhexyl)acetate → 11-[2,3-Difluorobiphenyl-4'-yl]oxyundecyl 2,2-bis(6-hydroxyhexyl)acetate
Reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][O:51]CC1C=CC=CC=1)[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=2[F:44])=[CH:33][CH:32]=1)=[O:17])C1C=CC=CC=1>[Pd].O1CCCC1>[OH:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=2[F:44])=[CH:33][CH:32]=1)=[O:17]Participants
4
Procedure
First, 4.9 g of 11-[2,3-difluorobiphenyl-4'-yl]oxyundecyl 2,2-bis(6-benzyloxyhexyl)acetate, 1.5 g of 10% Pd-C, and 100 ml of tetrahydrofuran were placed in a 300 ml autoclave. The mixture was stirred at room temperature for 2 days under a hydrogen pressure of 10 kg/cm2. The catalyst was filtered away and a filtrate was concentrated. Thereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=7/3) to obtain 3.7 g of 11-[2,3-difluorobiphenyl-4'-yl]oxyundecyl 2,2-bis(6-hydroxyhexyl)acetate (Y: 97.5%). The compound thus obtained had a purity of 98% by HPLC.
Workup
- filtrationThe catalyst was filtered away
- concentrationa filtrate was concentrated
- customThereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=7/3)
Sources & evidence
- ORD record
- ord-4bf99fe26be942499bc382ced393d979
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750213
Reaction notes
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