4-Hydroxy-3,5-bis(t-butyl)benzaldoxime → Benzonitrile, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-

HRID 843999Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[CH:8]=[N:9]O)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C.C(OCC)C>[C:15]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]=1[OH:14])[C:8]#[N:9])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3,5-Di-tert-butyl-4-hydroxy-benzaldehyde oxime (3.0 grams, 8.4 mmole) in acetic anhydride (6 ml) was was refluxed for 2 hours. The mixture was cooled to 0° C. and saturated sodium hydrogencarbonate was added. The mixture was extracted with methylene chloride. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to give a solid. This was dissolved in diethyl ether and extracted with 1 N sodium hydroxide which was then acidified to pH 1 and extracted with ethyl acetate. The extract was dried and concentrated to a yellow solid which was recrystalized from ethyl acetate/hexane to give white crystals (1.05 g). MW 231; MS (m/e) 249 (M++NH4+).

Workup

extractionThe mixture was extracted with methylene chloride
washThe combined extracts were washed with saturated NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a solid
extractionextracted with 1 N sodium hydroxide which
extractionextracted with ethyl acetate
customThe extract was dried
concentrationconcentrated to a yellow solid which
customwas recrystalized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-5c09e90a1c474adaa12a8a64284234f3
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380218B1

Reaction notes

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