Water → Benzonitrile, 3,5-dimethyl-4-(4-pentynyloxy)-

HRID 1681910Notes

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+].O>CN1CCCC1>[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, 32 ml 5-chloro-1-pentyne (d=0.968) and 74.63 g milled potassium carbonate in 25 ml N-methylpyrrolidine was heated under nitrogen at 100° C. with stirring for four hours. The mixture, after cooling to room temperature and addition of 300 ml water, was extracted with ethyl acetate. The ethyl acetate extracts were washed with aqueous 2N sodium hydroxide solution and saturated sodium chloride solution, dried (MgSO4) and then concentrated in vacuo. The residue was subjected to flash filtration (activated magnesium silicate; ether/hexane) and the filtrate was concentrated in vacuo to give, after recrystallization (methyl alcohol/0° C.) 34.64 g of the title compound.

Workup

temperatureThe mixture, after cooling to room temperature
extractionwas extracted with ethyl acetate
washThe ethyl acetate extracts were washed with aqueous 2N sodium hydroxide solution and saturated sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
filtrationThe residue was subjected to flash filtration (activated magnesium silicate; ether/hexane)
concentrationthe filtrate was concentrated in vacuo
customto give
customafter recrystallization (methyl alcohol/0° C.) 34.64 g of the title compound

Sources & evidence

ORD record: ord-8dc7b6e04ba64a2cbe75d6b15672e699
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175177

Reaction notes

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