N-Methylol-alpha-chloroacetamide → 2-Acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol

HRID 1389562Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].O[CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20])[C:5]=1[OH:14])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2.88 g of 2-acetyl-4-tert-butylphenol (prepared in Reference Example 2) dissolved in 20 ml of a mixed solution of glacial acetic acid and conc. sulfuric acid (10:1) were added 2.78 g of N-hydroxymethylchloroacetamide at room temperature and stirred at 60° C. for 2 hours. The reaction mixture was poured into 100 ml of ice-water, extracted with diethyl ether and the extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and ethyl acetate (50:1) as an eluting agent to give 3.83 g of the title compound having the following physical properties.

Workup

extractionextracted with diethyl ether
washthe extract was washed with water and saturated brine successively
dry with materialdried over magnesium sulfate anhydride
concentrationconcentrated at reduced pressure
customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record: ord-b650a8b2c1334530970227c7fc82ac9e
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04245099

Reaction notes

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