Sodium Cyanide → alpha-Hydroxy-2-nitro-3-phenylbenzofuran-7-acetonitrile

HRID 262223Notes

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].S(=O)(O)[O-].[Na+].[C-:26]#[N:27].[Na+].S(=O)(O)[O-]>O.C(Cl)(Cl)Cl.C(OCC)C>[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:26]#[N:27]

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 followed by 1.5 g. (0.030 mole) of sodium cyanide in 5 ml. of water after an additional 30 minutes. About 0.7 g. of sodium bisulfite is added 1.5 hours later, and the mixture is cooled to 0° C. 30 minutes after the bisulfite addition and maintained 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
temperaturemaintained for about 16 hours
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-5f6eddccb17c4d9986cbc52082debe2b
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153716

Reaction notes

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