Ethyl Acetate → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

HRID 1395124Notes

Reaction equation

[C-:1]#[N:2].[Na+].S(=O)(O)[O-].[O:8]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C>O.CN(C)C=O.C(O)(=O)C>[C:1]([CH:18]([OH:19])[C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:16]=1)#[N:2]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 0.765 Kg of sodium cyanide in 3.8 liters of water was added with stirring at 5° C. over 10 minutes to a mixture of 3.700 Kg of combination bisulfite of m-phenoxy-benzaldehyde (98% titer) in 7.4 liters of dimethylformamide and 3.8 liters of acetic acid were added thereto over 30 minutes at 5° C. The mixture was stirred for 30 minutes at 10° C. and the reaction mixture was then poured into a mixture of water and ethyl acetate. The mixture was stirred and decanted and the aqueous phase was extracted twice more with ethyl acetate. The combined ethyl acetate phases were washed with water, dried and stirred with 0.37 Kg of activated charcoal and 0.37 Kg of sodium sulfate. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 2.770 Kg of α-cyano-3-phenoxy-benzyl alcohol containing 1% of dimethylformamide.

Workup

additionwere added
stirringThe mixture was stirred
customdecanted
extractionthe aqueous phase was extracted twice more with ethyl acetate
washThe combined ethyl acetate phases were washed with water
customdried
stirringstirred with 0.37 Kg of activated charcoal and 0.37 Kg of sodium sulfate
filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-1cf01f86b10a41628f99d739cd81becd
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04202835

Reaction notes

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