O-Cresol → HCID 86751970, compound

HRID 726856Notes

Reaction equation

[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:11][CH2:12][O:13][N:14]=[C:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]Br)[C:16]([O:18][CH3:19])=[O:17].NC(N)=S.[Cl-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[F:11][CH2:12][O:13][N:14]=[C:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][O:7][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[CH3:8])[C:16]([O:18][CH3:19])=[O:17]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of 1.84 g of o-cresol in 15 ml of dimethylformamide is added dropwise at 20° C. to a suspension of 0.4 g of sodium hydride in 5 ml of dimethylformamide. After 3 hours a solution of 5.0 g of 2-(bromomethyl)-phenylglyoxalic acid methyl ester O-fluoromethyl oxime in 25 ml of dimethylformamide is added dropwise to the brown suspension. After 16 hours 0.3 g of thiourea is added thereto and the reaction mixture is heated at 30° C. for 0.5 hour. The reaction mixture is then poured onto a saturated sodium chloride solution and extraction is carried out with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields pure 2-(2-methylphenoxymethyl)-phenylglyoxalic acid methyl ester O-fluoromethyl oxime; m.p. 101°-102° C.

Workup

washThe combined organic phases are washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-0cc465395b6a4be78dd105532c2500a0
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710314

Reaction notes

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