HCID 54150769, compound → HCID 20499886, compound

HRID 851818Notes

Reaction equation

HRID 851818 reaction equation
[C:1]12[CH2:15][CH2:14][CH:13]=[C:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2>C1(C)C=CC=CC=1.[Pd]>[C:1]12[CH2:15][CH2:14][CH2:13][C:12]=1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2

Participants

4

Reactant 1

HCID 54150769HCID 54150769, compound

Product 1

HCID 20499886HCID 20499886, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

6.06 g of bicyclo[10.3.0]pentadec-1,12-diene--crude material; see Example 1--in 40 ml of toluene were hydrogenated at 100°, under atmospheric pressure, in the presence of 0.6 g of 10% palladium on charcoal. After 60 min. of hydrogenation, the reaction mixture was cooled, filtered on CELITE and finally distilled (0.02 Torr--bath temperature: 140°) to afford 5.2 g (84% yield) of the desired title compound having a purity of 93% according to vapour phase chromatography analysis (CARBOWAX 10%--1.6 m--140°). The compound thus prepared was found identical with a sample prepared according to J. Amer. Chem. Soc. 79, 5558 (1957).

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationfiltered on CELITE
  3. distillationfinally distilled (0.02 Torr--bath temperature: 140°)

Sources & evidence

ORD record
ord-a897dabd95a2422cac5c914a1a255fb5
Source dataset
uspto-grants-1983_05
Patent number
US04386220

Reaction notes

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