16-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate → 16-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-hydroxyhexyl)acetate

HRID 1289395Notes

Reaction equation

HRID 1289395 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][O:56]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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=2[F:49])=[CH:38][CH:37]=1)=[O:17])C1C=CC=CC=1>[Pd].O1CCCC1>[OH:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][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][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:43]=2[F:49])=[CH:40][CH:41]=1)=[O:17]

Participants

4

Reactant 1

HCID 1892085316-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate

Product 1

HCID 1892087316-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-hydroxyhexyl)acetateYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

First, 5.8 g of 16-[2,3-difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate, 1.8 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. A 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 3.9 g of 16-[2,3-difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-hydroxyhexyl)acetate (Y: 85.5%). The compound thus obtained had a purity of 99.2% by HPLC and an m.p. of 45.2° C. to 48.8° C.

Workup

  1. filtrationA catalyst was filtered away
  2. concentrationa filtrate was concentrated
  3. customThereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-253114c7ffaa462bba9aa8cf6e9a9e23
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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