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

HRID 1961489Notes

Reaction equation

HRID 1961489 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].[Cl:12][CH2:13][C:14]([NH:16][CH2:17]O)=[O:15].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:17][NH:16][C:14](=[O:15])[CH2:13][Cl:12])=[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-chloroacetamideYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 3-tert-butyl phenol (500.0 mg, 3.33 mmol) and 2-chloro-N-(hydroxymethyl)acetamide (411.2 mg, 3.33 mmol) was added in portions to an ice-bath cold solution of acetic acid (3.0 ml) and conc. H2SO4 (0.5 ml). The mixture was stirred at 0-5° C. for 3.0 h. and then it was allowed to warm to r.t. Stirring continued at r.t. for 20 h. The mixture was poured into ice-water, neutralized with solid NaHCO3 and extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (9:1→7:3) affording 278 mg (33%) the title compound.

Workup

  1. temperatureto warm to r.t
  2. stirringStirring
  3. waitcontinued at r.t. for 20 h
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a93edd84edd84cba80beaa554d3866ff
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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