Propargyl alcohol → HCID 19736363, compound

HRID 326217Notes

Reaction equation

[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13].[CH2:15]([OH:18])[C:16]#[CH:17].[OH-].[K+].[NH4+].[Cl-]>C1COCC1.O>[CH3:13][C:12]([OH:14])([CH2:11][CH2:10][C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[C:17]#[C:16][CH2:15][OH:18]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone (107 g, 0.55 mol) and propargyl alcohol (34 g, 0.61 mol) was added dropwise during 1.5 h to a mechanically stirred slurry of powered KOH (Fluka, 230 g, 4.1 mol) in THF (tetrahydrofuran 800 ml) maintained at 20° C. After a further 3 h, the brown mixture was poured into a cold solution of NH4Cl (250 g, 4.7 mol) in H2O (800 ml) and the phases separated. Extraction of the aqueous phase with ether and concentration of the combined organic phase afforded a reddish brown solid which was recrystallized from petroleum ether (80/100) to furnish 4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-hexyn-1,4-diol as a pale yellow powder (110 g, 80% yield).

Workup

customthe phases separated
extractionExtraction of the aqueous phase with ether and concentration of the combined organic phase
customafforded a reddish brown solid which
customwas recrystallized from petroleum ether (80/100)

Sources & evidence

ORD record: ord-00d63733f46d46a6b7d1b2e0815978e9
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268355

Reaction notes

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