Thionyl Chloride → 3,3-Bis(2-methoxyphenyl)-2-propenenitrile

HRID 2232802Notes

Reaction equation

S(Cl)(Cl)=O.O[C:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[CH2:7][C:8]#[N:9]>N1C=CC=CC=1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])=[CH:7][C:8]#[N:9]

Participants

Conditions

Temperature: 10 °C

Procedure

Thionyl chloride (4.5 mL) was added to a stirred suspension of beta-hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile 13.45 g) in dry pyridine (70 mL) maintained at 10° C. during the addition. The reaction was stirred at room temperature for 2 hours, then was diluted with ice-water and extracted with dichloromethane. The organic extract was washed with 3N HCl (1×150 mL; 1×20 mL) and brine and then was dried (MgSO4) and evaporated. The residue was crystallized from isopropanol-hexane to provide 9.0 g of 3,3-bis(2-methoxyphenyl)-2-propenenitrile, mp 99°-100° C. a portion from the same solvents afforded the analytical sample, mp 100.5°-101.5° C.

Workup

extractionextracted with dichloromethane
extractionThe organic extract
washwas washed with 3N HCl (1×150 mL; 1×20 mL) and brine
dry with materialwas dried (MgSO4)
customevaporated
customThe residue was crystallized from isopropanol-hexane

Sources & evidence

ORD record: ord-73d051088efa433db7f5fe4204730f9f
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788206

Reaction notes

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