2-Nitrobenzoic acid → Tert-butyl 2-nitrobenzoate

HRID 2164680노트

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HRID 2164680 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]>S(Cl)(Cl)=O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][C:5]([CH3:9])([CH3:6])[CH3:4])=[O:7])([O-:3])=[O:2]

참가 물질

3

반응물 1

HCID 110872-Nitrobenzoic acid

생성물 1

HCID 4860715Tert-butyl 2-nitrobenzoate수율 141.3%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

A mixture of 2-nitrobenzoic acid (25.0 g.) and thionyl chloride (50 ml.) was refluxed for an hour and then evaporated. To the residue was added benzene (125 ml.) followed by removal of benzene. To the residue were added benzene (125 ml.), pyridine (23.7 g.) tert-butyl alcohol (22.2 g.) under ice-cooling and then the resulting solution was refluxed under heating for 2 hours. The reaction mixture was poured into ice water. The benzene layer was separated, washed successively with water, 1N aqueous solution of sodium hydroxide (twice), water 1M aqueous solution of citric acid (twice), water and an aqueous solution of sodium chloride, dried over magnesium sulfate and then teated with activated charcoal. Thus obtained organic layer was chromatographed on silica gel (150 g.) eluting with a mixture of benzene and n-hexane (1:1) to give a yellowish oil of the title compound (23.6 g.)

후처리

  1. temperaturewas refluxed for an hour
  2. customevaporated
  3. additionTo the residue was added benzene (125 ml.)
  4. customfollowed by removal of benzene
  5. additionTo the residue were added benzene (125 ml.), pyridine (23.7 g.) tert-butyl alcohol (22.2 g.) under ice-
  6. temperaturecooling
  7. temperaturethe resulting solution was refluxed
  8. temperatureunder heating for 2 hours
  9. additionThe reaction mixture was poured into ice water
  10. customThe benzene layer was separated
  11. washwashed successively with water, 1N aqueous solution of sodium hydroxide (twice), water 1M aqueous solution of citric acid (twice), water
  12. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulfate
  13. customThus obtained organic layer was chromatographed on silica gel (150 g.)
  14. washeluting with a mixture of benzene and n-hexane (1:1)

출처 및 근거

ORD 기록
ord-8a752f45469e42dc953fc2de77f2a17e
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04506076

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