tert-Butyl methyl ether → 3-Nitrophthalic anhydride

HRID 1670396Notes

Reaction equation

HRID 1670396 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1[C:13]([OH:15])=[O:14])([O-:3])=[O:2].COC(C)(C)C>C(OC(=O)C)(=O)C>[N+:1]([C:4]1[C:5]2[C:13](=[O:14])[O:15][C:7](=[O:9])[C:6]=2[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 690433-Nitrophthalic acid

Product 1

HCID 216313-Nitrophthalic anhydrideYield 88.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 474.8 g (2.25 mol) of 3-nitrophthalic acid in 450 ml of acetic anhydride was stirred under reflux for 1 h. The solution was slowly cooled to 80° C. Then 1000 ml of methyl-tert-butyl ether (MTBE) were added expeditiously and the solution was cooled to 15° C. The resulting solid was isolated, washed with MTBE and dried in a vacuum oven at 40° C. Yield: 88.8%

Workup

  1. temperatureunder reflux for 1 h
  2. temperaturethe solution was cooled to 15° C
  3. customThe resulting solid was isolated
  4. washwashed with MTBE
  5. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-e9f30dbbb1314533a1f4fda75db2f612
Source dataset
uspto-grants-2011_08
Patent number
US07994160B2

Reaction notes

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