Phthalic Acid → Benzoic Acid

HRID 1416521Notes

Reaction equation

HRID 1416521 reaction equation
[C:1]1(C(O)=O)[C:2]([C:7]([OH:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O.CC(C)=O>[C:7]([OH:9])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=1

Participants

7

Reactant 4

HCID 1017Phthalic AcidHCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,2-benzenedicarboxylic acid, 4-bromo, 2-methyl ester and 1,2-benzenedicarbocylic acid, 4-bromo, 1-methyl ester (2.07 g; 8 mmol), triethylamine (6.0 ml; 0.043 mol), and toluene (80 ml) was added diphenylphosphoryl azide (5.0 g; 0.018 mol). The reaction mixture was heated at 80° C. for 2 hours at which time acetone (200 ml) and water (40 ml) was added. The reaction mixture was heated further at 80° C. for 8 hours, cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexane) to provide benzoic acid, 2-amino-4-bromo, methyl ester (0.514 g, as a white solid) and benzoic acid, 2-amino-5-bromo, methyl ester (0.930 g, as a white solid).

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d752aa3d40bb4f99b52a6ba12407f798
Source dataset
uspto-grants-1999_06
Patent number
US05914327

Reaction notes

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