HCID 67639801, compound → HCID 18920851, compound

HRID 1289410Notes

Reaction equation

HRID 1289410 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44]CC2C=CC=CC=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30]CC2C=CC=CC=2)=[CH:11][CH:10]=1>[Pd].O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 67639801HCID 67639801, compound

Product 1

HCID 18920851HCID 18920851, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

First, 3.3 g of 2,3-difluoro-4'-[8,8-bis(6-benzyloxyhexyl)-6-octene-1-yl]oxybiphenyl, 1 g of 10% Pd-C, and 100 ml of tetrahydrofuran were placed in a 200 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=3/2) to obtain 2.3 g of 2,3-difluoro-4'-[8,8-bis(6-hydroxyhexyl)octyl]oxybiphenyl (Y: 93.6%). The compound thus obtained had a purity of 98.8% by HPLC.

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=3/2)

Sources & evidence

ORD record
ord-c59e031962cb478a800d8c9b129cb0ed
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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