Phthalic Anhydride → HCID 54083732, compound

HRID 1651180Notes

Reaction equation

HRID 1651180 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH2:30]([O:29][C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:12]1[CH:13]=[CH:14][C:15]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[CH:16][CH:17]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 12824183HCID 12824183, compound

Product 1

HCID 54083732HCID 54083732, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

At 0°-3° C., 9.6 g of phthalic anhydride are added to a solution of 18 g of ethyl 10-phenyldecanoate in 100 ml of 1,2-dichloroethane, after which 26 g of aluminium chloride are added in portions over a period of 1 hour. After stirring for 20 hours at room temperature, the mixture is poured onto ice/2N hydrochloric acid and extracted with methylene chloride. Washing of the organic phase with saturated sodium chloride solution, drying and evaporation gives 25.1 g of 2-[4'-(9"-ethoxycarbonylnonyl)benzoyl]benzoic acid as a waxy solid which can be used for the next step without purification.

Workup

  1. additionthe mixture is poured onto ice/2N hydrochloric acid
  2. extractionextracted with methylene chloride
  3. washWashing of the organic phase with saturated sodium chloride solution
  4. customdrying
  5. customevaporation

Sources & evidence

ORD record
ord-cecdea2ad7924ce58c6d511f017b4eff
Source dataset
uspto-grants-1990_05
Patent number
US04927865

Reaction notes

Loading…