2-Nitrobenzoic acid → Tert-butyl 2-nitrobenzoate

HRID 745705Notes

Reaction equation

HRID 745705 reaction equation
[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]

Participants

3

Reactant 1

HCID 110872-Nitrobenzoic acid

Product 1

HCID 4860715Tert-butyl 2-nitrobenzoateYield 141.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

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.)

Workup

  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)

Sources & evidence

ORD record
ord-127d91ef7afa4968b0882cab16e8056d
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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