O-Xylene → HCID 15044333, compound

HRID 974360Notes

Reaction equation

HRID 974360 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[C:8]([C:12]1[CH:13]=[C:14]([CH2:23][CH2:24][C:25]([NH:27][NH2:28])=[O:26])[CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])([CH3:11])([CH3:10])[CH3:9].C1(C)C(C)=CC=CC=1>O>[C:19]([C:16]1[CH:15]=[C:14]([CH2:23][CH2:24][C:25]([NH:27][N:28]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:6])=[O:26])[CH:13]=[C:12]([C:8]([CH3:9])([CH3:10])[CH3:11])[C:17]=1[OH:18])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7923Maleic AnhydrideHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazide

Product 1

HCID 15044333HCID 15044333, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of maleic anhydride (4.9 g, 50.0 mmol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (15.2 g, 50.0 mmol) and 250 ml of xylene was refluxed for one hour under a nitrogen atmosphere with the azeotropic removal of water. The solvent was then removed on a rotary evaporator. The residual mass was extracted with 100 ml of tetrahydrofuran and the extract was added to 500 ml of hexane to precipitate the product. The product was collected by filtration and air dried. 16.1 g of a solid material was obtained having a melting range of 90°-94° C.

Workup

  1. customThe solvent was then removed on a rotary evaporator
  2. extractionThe residual mass was extracted with 100 ml of tetrahydrofuran
  3. additionthe extract was added to 500 ml of hexane
  4. customto precipitate the product
  5. filtrationThe product was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-f8ab4b533d6643cfab74bf6fe5efa93d
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Reaction notes

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