Methane → Butanal, 4-(acetyloxy)-2-methylene-

HRID 1703504Notes

Reaction equation

HRID 1703504 reaction equation
C([O:4][CH2:5][CH:6]=[CH:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])(=O)C.[CH4:13]>C1C=CC=CC=1.[Rh]>[CH:5]([C:6]([CH2:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])=[CH2:13])=[O:4]

Participants

5

Reactant 2

HCID 297MethaneHCID 1404022-Butene-1,4-diol diacetate

Product 1

HCID 11083989Butanal, 4-(acetyloxy)-2-methylene-Yield 54%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 241BenzeneSolvent

Procedure

The procedure of Example 7 was repeated using 1,4-diacetoxy-2-butene (170 g.) and 5% by weight rhodium on 95% by weight charcoal (1.12 g.) in benzene (340 g.). The reaction took 6 hours to go to completion. Work-up in the manner of Example 7 gave a 54% yield of 2-formyl-4-acetoxybutene.

Sources & evidence

ORD record
ord-b3e7fe979de14ed89e8e6ef60d30d599
Source dataset
uspto-grants-1978_11
Patent number
US04124619

Reaction notes

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