Sodium Cyanide → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

HRID 443767Notes

Reaction equation

[Na].[OH:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)S(O)(=O)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[C-:30]#[N:31].[Na+]>O>[C:30]([CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[OH:2])#[N:31]

Participants

Conditions

Temperature: 15 °C

Procedure

Into a flask were placed 755.7 g (2.5 moles) of the sodium salt of (hydroxy)(3-phenoxyphenyl)methanesulfonic acid, 237.6 g (1.25 moles) of sodium metabisulfite, and 2273 ml of water. The flask was cooled to 15° C. and a solution of 245.1 g (5.0 moles) of sodium cyanide in 302 ml of water was added dropwise. The reaction mixture was allowed to warm to room temperature, was stirred for 3 hours, then extracted three times with 800 ml of diethyl ether. The extract was washed once with 800 ml of a solution of 25% sodium metabisulfite and 1 N hydrochloric acid and twice with distilled water. After being dried over magnesium sulfate, the ether was evaporated, leaving a residue of 498.5 g of 94% (cyano)(3-phenoxyphenyl)methanol by gc analysis.

Workup

customInto a flask were placed
temperatureto warm to room temperature
extractionextracted three times with 800 ml of diethyl ether
washThe extract was washed once with 800 ml of a solution of 25% sodium metabisulfite and 1 N hydrochloric acid and twice with distilled water
dry with materialAfter being dried over magnesium sulfate
customthe ether was evaporated

Sources & evidence

ORD record: ord-06e7200e54a346e0a9b19f215959fad8
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04261921

Reaction notes

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