Potassium Carbonate → Benzonitrile, 3,5-dimethyl-4-(4-pentynyloxy)-

HRID 1681925Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[C:5]#[N:6].Cl[CH2:13][CH2:14][CH2:15][C:16]#[CH:17].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[O:10][CH2:17][CH2:16][CH2:15][C:14]#[CH:13])[C:5]#[N:6]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 40 g 3,5-dimethyl-4-hydroxybenzonitrile, 30.77 g 1-chloro-4-pentyne, 74.63 g potassium carbonate and 130 ml N-methylpyrrolidinone was heated with stirring to 100° C. and stirring was continued at 100° C. for 4 hrs. The mixture was cooled to room temperature and 800 ml of water was added. This mixture was extracted with 400 ml ethyl acetate and the extract was washed with 2N sodium hydroxide and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting black oil, dissolved in ethyl acetate, was passed through a pad of florisil to remove the color and the filtrate was concentrated in vacuo. The residue was recrystallized from methyl alcohol to yield 34.64 g (60.2%) of 3,5-dimethyl-4-(3-ethynylpropoxy)benzonitrile, m.p. 48°-49° C.

Workup

temperaturewas heated
stirringstirring
temperatureThe mixture was cooled to room temperature
extractionThis mixture was extracted with 400 ml ethyl acetate
washthe extract was washed with 2N sodium hydroxide and saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
dissolutionThe resulting black oil, dissolved in ethyl acetate
customto remove the color
concentrationthe filtrate was concentrated in vacuo
customThe residue was recrystallized from methyl alcohol

Sources & evidence

ORD record: ord-ec238934f1e54a179f201bf5e8f4d157
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175178

Reaction notes

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