Phthalic Anhydride → HCID 9801621, compound

HRID 1645885Notes

Reaction equation

HRID 1645885 reaction equation
[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=1.[C:21]1(=O)[O:26][C:24](=[O:25])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12>C1(C)C=CC=CC=1>[O:25]=[C:24]1[C:23]2[C:22](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21](=[O:26])[N:1]1[C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:15])([CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 15068117HCID 15068117, compound

Product 1

HCID 9801621HCID 9801621, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.8 g (10 mmol) of 5-(4-amino-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid, methyl ester as the free base (Example 2) and 1.5 g (10 mmol) of phthalic anhydride in 100 mL of toluene is stirred at reflux beneath a phase separating head for 2 hours. The solvent is removed and on standing a red brown oil crystallizes. Recrystallization from isoctaneisopropyl ether with the addition of charcoal affords 2.8 g of the title compound as pale pink crystals; mp 109°-111° C.

Workup

  1. temperatureat reflux beneath a phase
  2. customseparating head for 2 hours
  3. customThe solvent is removed
  4. customcrystallizes
  5. customRecrystallization from isoctaneisopropyl ether
  6. additionwith the addition of charcoal

Sources & evidence

ORD record
ord-eb2239e1869f4a28a8548726a9d75cba
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

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