Acetone → 6,10-Dimethylundeca-3-en-2-on-10-ol

Reaction equation

[CH3:1][CH:2]([CH2:10][CH:11]=O)[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].C#C.[CH3:15][C:16]([CH3:18])=[O:17]>>[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][C:6]([CH3:7])([OH:9])[CH3:8])[CH2:10][CH:11]=[CH:15][C:16](=[O:17])[CH3:18]

Participants

Reactant 3

HCID 180Acetone

HCID 6326Acetylene

HCID 7888Hydroxycitronellal

Product 1

HCID 537842226,10-Dimethylundeca-3-en-2-on-10-ol

Procedure

The ethynylation of 212 g of 6,10-dimethylundeca-3-en-2-on-10-ol obtained by aldol condensation of hydroxycitronellal and acetone with acetylene was worked out in the same manner as in example 9 except that hydroxycitronellal was used in place of pseudoionone and 269 g of a crude product was thus obtained.

Sources & evidence

ORD record: ord-1495c08bc8c4420b89756e5507cd2bdf
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03981930

Reaction notes

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