Cinnamoylbenzene → Nonane

HRID 2050404Notes

Reaction equation

HRID 2050404 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C.C(=CC(C1C=CC=CC=1)=O)C1C=CC=CC=1>CN1CCCC1=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 7189CinnamoylbenzeneHCID 81741-Decanol

Product 1

HCID 8141NonaneYield 16.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

In a typical combined dehydrogenation/decarbonylation, 1-decanol (398 μmol) was treated with RuCl2 (PPh3)3 (19 μmol), RhCl(PPh3)3 (96 pmol) and benzalacetophenone (438 pmol) in 2 ml of N-methyl-2-pyrrolidinone and heated under nitrogen at 125° C. After 40 hours, 64 μmol of nonane had formed; after 6 days the yield of nonane was 92 μmol (96% based on Rh).

Sources & evidence

ORD record
ord-8eea5c4e2ce241da80721c80f1fea3b2
Source dataset
uspto-grants-1991_05
Patent number
USH0000918

Reaction notes

Loading…