Sulfuric Acid → 2-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

HRID 733301

반응식

HRID 733301 반응식
[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(=O)C[Cl:21].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[ClH:21].[NH2:18][CH2:17][C:8]1[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[OH:15]

참가 물질

6

반응물 4

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

생성물 1

HCID 452597712-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23a49715451e4796a490a7c68dc6fa5b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589127B2

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