Water → Trimellitic acid

HRID 874798

Reaction equation

HRID 874798 reaction equation
[CH:1]1[C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]2[C:10]([O:12][C:13](=[O:14])[C:3]=2[CH:2]=1)=[O:11].C1(=O)[O:21]CCCCC1.N1C=CC=CC=1.[OH2:29]>CC(C)=O>[C:13]([OH:12])(=[O:14])[C:3]1[C:4](=[CH:5][C:6](=[CH:1][CH:2]=1)[C:7]([OH:21])=[O:8])[C:10]([OH:11])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10401epsilon-CAPROLACTONEHCID 70998Trimellitic anhydride chloride

Product 1

HCID 10708Trimellitic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Trimellitic acid anhydride chloride (50 g, 0.240 mol) is dissolved in 150 mL acetone in a 3-neck flask under nitrogen. The flask is cooled in an ice bath. A solution of AFM-caprolactone intermediate (82.05 g, 0.12 mol), and pyridine (19.0 g, 0.240 mol) in 80 ml of acetone is added slowly through a dropping funnel while continuously stirring the cold solution. After addition is completed, the flask contents are continuously stirred at room temperature for 4 hours. Water (4.32 g, 0.240 mol) is added and the solution is stirred continuously at room temperature overnight. The solids formed are removed by vacuum filtration and washed with acetone. The filtrate is concentrated and dried to yield the product

Workup

  1. temperatureThe flask is cooled in an ice bath
  2. additionAfter addition
  3. stirringthe flask contents are continuously stirred at room temperature for 4 hours
  4. stirringthe solution is stirred continuously at room temperature overnight
  5. customThe solids formed
  6. customare removed by vacuum filtration
  7. washwashed with acetone
  8. concentrationThe filtrate is concentrated
  9. customdried
  10. customto yield the product

Sources & evidence

ORD record
ord-4b02020fe8c24bd496cc7c2cae3b665e
Source dataset
uspto-grants-2015_03
Patent number
US08980969B2

Linked notes

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