Sulfuric Acid → 4-Phenoxybenzoyl chloride

HRID 1648668Notes

Reaction equation

HRID 1648668 reaction equation
C(Cl)(=O)[C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:8])=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].CN([CH:20]=[O:21])C.S(=O)(=O)(O)O>O(C1C=CC(C(=O)C2C=CC=CC=2)=CC=1)C1C=CC=CC=1.ClCCCl>[O:21]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([Cl:8])=[O:7])=[CH:9][CH:10]=1)[C:20]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 741934-Phenoxybenzoyl chlorideYield 1,905.3%

Reagents, catalysts & solvents 2

HCID 2386234-PhenoxybenzophenoneCatalystHCID 111,2-DichloroethaneSolvent

Procedure

p-Phenoxybenzoyl chloride (12.633 g, 0.0543 moles) and BPBPTCDI (3.5459 g, 0.0054 moles) were polymerized with terephthaloyl chloride (1.1572 g, 0.0057 moles) in the presence of aluminum chloride (32.84 g, 0.2463 moles), DMF (10.08 mLs, 0.1308 moles), p-phenoxybenzophenone (0.1646 g, 0.0006 moles) and DCE (120 mLs) initially at -30° C., but warming to room temperature over two hours. The reaction mixture was left at room temperature for fifteen hours and then heated at 28°-32° C. for twenty-six hours. After working up as described in Example 4 the copolymer was obtained as a very pale orange fibrous powder (14.33 g, 95.2% yield), IV 0.90 dl/g (c=0.12 g/dL).

Workup

  1. waitThe reaction mixture was left at room temperature for fifteen hours
  2. temperatureheated at 28°-32° C. for twenty-six hours

Sources & evidence

ORD record
ord-a38cbcc1db1e418dba150219cb11ea41
Source dataset
uspto-grants-1995_07
Patent number
US05436310

Reaction notes

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