(+)-4-Benzyloxy-1-(1-hexyloxy-2,2,2-trifluoroethyl)benzene → (+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)phenol

HRID 2254947Notes

Reaction equation

HRID 2254947 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[CH2:21]([O:20][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[C:16]([F:17])([F:18])[F:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 1

HCID 19738677(+)-4-Benzyloxy-1-(1-hexyloxy-2,2,2-trifluoroethyl)benzene

Product 1

HCID 19738679(+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)phenolYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.1 g (3 mmol) of the product (9-1) of Preparation Example 2 was dissolved in a mixture of 80 ml of tetrahydrofuran and 20 ml of methanol, and the solution was added with 0.2 g of 10% Pd/C and stirred vigorously under hydrogen pressure of 1-1.2 atm. for 8 hours. After the reaction, Pd/C was filtered out and the filtrate was concentrated to obtain 0.82 g of (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)phenol (3-1). Yield: 99%; [α]D20 =+44.0° (c=1, CHCl3).

Workup

  1. filtrationwas filtered out
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f8f75c4381df483991112c9168d0da80
Source dataset
uspto-grants-1993_08
Patent number
US05238598

Reaction notes

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