2-Nitrobenzoic acid → Tert-butyl 2-nitrobenzoate

HRID 2231419ノート

反応式

HRID 2231419 の反応式
[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]

参加物

3

反応物 1

HCID 110872-Nitrobenzoic acid

生成物 1

HCID 4860715Tert-butyl 2-nitrobenzoate収率 141.3%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

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 treated 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.)

後処理

  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. additiontreated with activated charcoal
  14. customThus obtained organic layer was chromatographed on silica gel (150 g.)
  15. washeluting with a mixture of benzene and n-hexane (1:1)

出典と根拠

ORDレコード
ord-20153d66d69d433f87b6b573de141936
出典データセット
uspto-grants-1988_11
特許番号
US04782158

反応ノート

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