Sulfuric Acid → 2-Chloro-N-(2,4-di-tert-butyl-6-hydroxybenzyl)acetamide

HRID 1173300Notes

Reaction equation

HRID 1173300 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O[CH2:17][NH:18][C:19](=[O:22])[CH2:20][Cl:21].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:21][CH2:20][C:19]([NH:18][CH2:17][C:6]1[C:7]([OH:15])=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 62466N-Methylol-alpha-chloroacetamideHCID 708253,5-Di-tert-butylphenolHCID 516892Sodium Bicarbonate

Product 1

HCID 687174522-Chloro-N-(2,4-di-tert-butyl-6-hydroxybenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A finely powdered mixture of 5.2 g (25 mmol) of 3,5-di-tert-butylphenol and 3.15 g (25 mmol) of N-hydroxymethyl-2-chloroacetamide was added in portions to a vigorously stirred solution of 22.5 mL acetic acid and 2.5 mL (98%) sulfuric acid at 0-10° C. The reaction mixture was allowed to warm to room temperature over several hours, and stirring was maintained for a total of 16 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 15-30-50% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. temperaturewas maintained for a total of 16 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 15-30-50% EtOAc in hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-ac2ef96240094409a07cf1e82d944baa
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

Loading…