Hydrochloric Acid → 1-cyclohexyl-1-phenylprop-2-yn-1-ol

HRID 1087664Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium acetylide (47.84 g, 0.52 mole) was added to 70 ml of THF. The solution was cooled to 0° C. and a solution of cyclohexyl phenyl ketone in 100 ml of THF was added over a period of 15 minutes with stirring. The solution was allowed to warm to room temperature and stirred for 16 hours. The solution was then cooled to 0° C. and 50 ml of a 5N HCl was added. The solution was then warmed to room temperature and 200 ml of water was added. The solution was transferred to a separatory funnel and washed with ether. The ether washes were combined and dried. Upon removal of the ether under vacuum and vacuum distillation of the crude product a pale yellow oil was isolated (60.33 g, 82.9%): bp 111°-4° C. (0.8 mm), NMR (CDCl3) δ7.7-7.2(m, 5H), 2.6(s, 1H), 2.3(s, 1H), 2.1-0.9(m, 11H). IR (neat) 3433, 3304, 2111, 1448, 1016 cm-1.

Workup

temperatureto warm to room temperature
stirringstirred for 16 hours
temperatureThe solution was then cooled to 0° C.
temperatureThe solution was then warmed to room temperature
customThe solution was transferred to a separatory funnel
washwashed with ether
customdried
customUpon removal of the ether
distillationunder vacuum and vacuum distillation of the crude product a pale yellow oil
customwas isolated (60.33 g, 82.9%)

Sources & evidence

ORD record: ord-aba5325043c84dd0bdd05eea942bef57
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036107

Reaction notes

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