Sulfuric Acid → N-(4-tert-butyl-2-hydroxybenzyl)-2-chloroacetamide

HRID 1173295Notes

Reaction equation

HRID 1173295 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O[CH2:13][NH:14][C:15](=[O:18])[CH2:16][Cl:17].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][Cl:17])=[C:7]([OH:11])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 62466N-Methylol-alpha-chloroacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 66746309N-(4-tert-butyl-2-hydroxybenzyl)-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A finely powdered mixture of 15 g (0.10 mol) of 3-tert-butylphenol and 12.4 g (0.10 mol) of N-hydroxymethyl-2-chloroacetamide was added in portions to a vigorously stirred solution of 90 mL acetic acid and 10 mL (98%) sulfuric acid at 0° C. The reaction mixture was allowed to warm to room temperature over several hours, and stirring was maintained for a total of 20 hours. The reaction mixture was poured into ice-water, neutralized with saturated aqueous NaHCO3 solution and extracted into CH2Cl2. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 10-30% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. temperaturewas maintained for a total of 20 hours
  2. extractionextracted into CH2Cl2
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 10-30% EtOAc in hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-72a6e4d54eec459abaa7566e8228694e
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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