Diethyl Ether → alpha-Hydroxy-2-nitro-3-phenylbenzofuran-7-acetonitrile

HRID 614103Notes

Reaction equation

[N+:1]([C:4]1[O:5][C:6]2[C:18]([CH:19]=[O:20])=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2].C(OCC)C.S(=O)(O)[O-].[Na+].[C-:31]#[N:32].[Na+]>O.C(Cl)(Cl)Cl>[OH:20][CH:19]([C:18]1[C:6]2[O:5][C:4]([N+:1]([O-:3])=[O:2])=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:7]=2[CH:15]=[CH:16][CH:17]=1)[C:31]#[N:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 2.7 g. (0.010 mole) of 2-nitro-3-phenylbenzofuran-7-aldehyde and 20 ml. of diethyl ether is treated with 1.6 g. (0.015 mole) of sodium bisulfite in 10 ml. of water. After 30 minutes, 30 ml. of chloroform is added and then, 30 minutes later, 1.5 g. (0.030 mole) of sodium cyanide in 5 ml. of water is added. One-half hour after that 0.7 g. of sodium bisulfite is added, then, after another 30 minutes, the mixture is cooled at 0° C. for about 16 hours. The organic layer is separated, washed with aqueous sodium bisulfite solution, then with water, and dried over magnesium sulfate. Evaporation of the solution provides a solid which is recrystallized from a chloroform-heptane mixture to provide yellow crystals of α-hydroxy-2-nitro-3-phenylbenzofuran-7-acetonitrile, m.p. 137°-139° C.

Workup

additionA stirred mixture of 2.7 g
custom30 minutes
customOne-half hour
waitafter another 30 minutes
customThe organic layer is separated
washwashed with aqueous sodium bisulfite solution
dry with materialwith water, and dried over magnesium sulfate
customEvaporation of the solution
customprovides a solid which
customis recrystallized from a chloroform-heptane mixture

Sources & evidence

ORD record: ord-12e0b3ab466d434789a64fac5a1d5d3e
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04143154

Reaction notes

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