2-Methoxypropene → HCID 53863923, compound

HRID 1462837Notes

Reaction equation

HRID 1462837 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH:7]=[C:8]([CH3:11])[CH2:9][CH3:10])[C:3]#[CH:4].C[O:14][C:15]([CH3:17])=[CH2:16]>>[CH3:1][C:2]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:11])[CH2:9][CH3:10])=[CH:3][CH:4]=[CH:16][C:15](=[O:14])[CH3:17]

Participants

3

Reactant 2

HCID 83002-MethoxypropeneHCID 911336-Nonen-1-yn-3-ol, 3,7-dimethyl-

Product 1

HCID 53863923HCID 53863923, compound

Procedure

The acid-catalysed reaction of 3,7-dimethyl-non-1-yn-6-en-3-ol with isopropenyl methyl ether and subsequent base-catalysed isomerisation of the resulting β-keto-allene [see G. Saucy, R. Marbet, Helv. 50, 1158 (1967)] yielded in good yield 6,10-dimethyl-dodeca-3,5,9-trien-2-one which was cyclised in a known manner [see H. Rouve, M. Stoll, Helv. 30, 2216 (1947)] with 85% phosphoric acid to give 12/13-methyl-α-ionone. Subsequent reduction with lithium aluminium hydride gave 12/13-methyl-α-ionol.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-5d3cd7b3a1114dec82979f3753d53c56
Source dataset
uspto-grants-1984_07
Patent number
US04461309

Reaction notes

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