Ethanol → HCID 178520594, compound

HRID 1289401Notes

Reaction equation

HRID 1289401 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]CC2C=CC=CC=2)[CH2:11][CH2:10]1.C(O)C>[Pd].C(OCC)(=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 702EthanolHCID 178505692HCID 178505692, compound

Product 1

HCID 178520594HCID 178520594, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

First, 10.9 g of 2,3-difluoro-1-[trans-4-{13-benzyloxy-1-tridecenyl}cyclohexyl]benzene, 1 g of 10% Pd-C, 50 ml of ethanol, and 50 ml of ethyl acetate were placed in a 500 ml autoclave. The mixture was stirred at room temperature for 5 days under a hydrogen pressure of 8 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=4/1) and recrystallized from acetone to obtain 5.7 g of 2,3-difluoro-1-[trans-4-(13-hydroxytridecyl)cyclohexyl]benzene (Y: 64%). The compound thus obtained had a purity of 97.2% by GC and 99.8% 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=4/1)
  4. customrecrystallized from acetone

Sources & evidence

ORD record
ord-5abbee8b4e73442e989a237a94d08e55
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

Loading…