HCID 3359346, compound → HCID 22293131, compound

HRID 1377134Notes

Reaction equation

HRID 1377134 reaction equation
[C:1]1([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1>C1COCC1.[Pd]>[C:11]1([CH2:10][CH2:9][C:1]2[CH:2]=[CH:3][C:4]([CH2:7][OH:8])=[CH:5][CH:6]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 3359346HCID 3359346, compound

Product 1

HCID 22293131HCID 22293131, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenating 10 g (48 mmol) of 4-stilbenemethanol (Aldrich; Milwankee/U.S.A.) in 100 ml of THF, in the presence of 0.5 g of 5% Pd/C under low pressure and at RT, filtering through ®Celite (filtering aid based on kieselguhr, Johns-Manville Corp., obtainable from Fluka, Buchs, Switzerland) and evaporating the filtrate affords the title compound, approximately 15% of which, according to the 1H-NMR spectrum, consists of p-(2-phenylethyl)toluene: TLC Rf (A)=0.62; 1H-NMR (200 MHz, CDCl3): 2.92 (s, 4H), 4.68 (s, 2H), 7.15-7.35 (m, 9H).

Workup

  1. customevaporating the filtrate

Sources & evidence

ORD record
ord-c6f680f940e848038b9f11429151140d
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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