Cyclohexene → HCID 13320183, compound

HRID 544093Notes

Reaction equation

HRID 544093 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH:10]([OH:24])[CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:14]=2[C:15]#[N:16])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].C1CCCCC=1>C(O)C.[Pd]>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH:10]([OH:24])[CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[C:14]=2[C:15]#[N:16])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 133201822-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-6-nitrobenzonitrile

Product 1

HCID 13320183HCID 13320183, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10 g of 2-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-6-nitrobenzonitrile, 2.5 g 10% Pd on carbon and 10 g cyclohexene in 500 ml absolute ethanol is refluxed for 30 min. The reaction mixture is cooled to room temperature, filtered through Celite and freed of solvent. Trituration with diethyl ether and drying of the insolubles gives 6.1 g of the title compound as a white solid, m.p. 123°-125° C.

Workup

  1. filtrationfiltered through Celite
  2. dry with materialTrituration with diethyl ether and drying of the insolubles

Sources & evidence

ORD record
ord-10959c58f20c4a72a4aaf188727f3ff3
Source dataset
uspto-grants-1984_05
Patent number
US04448729

Reaction notes

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