Ethanol → HCID 178520594, compound

HRID 726492Notes

Reaction equation

HRID 726492 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=2[F:35])[CH2:24][CH2:23]1)C1C=CC=CC=1.C(O)C>C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]1[CH2:23][CH2:24][C@H:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=2[F:35])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 702EthanolHCID 178505692HCID 178505692, compound

Product 1

HCID 178520594HCID 178520594, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

First, 10.9 g of 1-[trans-4-{13-benzyloxy-1-tridecenyl}cyclohexyl]-2,3-difluorobenzene, 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 1-[trans-4-(13-hydroxytridecyl)cyclohexyl]-2,3-difluorobenzene (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-3e63ed569483476da8520aa53e820550
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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