O-Xylene → HCID 13772097, compound

HRID 980929Notes

Reaction equation

HRID 980929 reaction equation
C1(C)C(C)=CC=CC=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:17]([N:24]=[CH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)C2C=CC=CC=2)[CH:14]=[CH:15][CH:16]=1.[C:32]1(=[O:38])[O:37][C:35](=[O:36])[CH2:34][CH2:33]1>CCOCC>[CH2:25]([N:24]1[C:35](=[O:36])[CH2:34][CH:33]([C:32]([OH:37])=[O:38])[CH:17]1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7922Succinic anhydrideHCID 70420420HCID 70420420, compound

Product 1

HCID 13772097HCID 13772097, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 450 ml. of xylene was added 143.3 gm of 3-methoxyphenylbenzylidenebenzylamine and 63.9 gm. of succinic anhydride. The solution was refluxed for 15 hours, cooled and extracted with saturated sodium bicarbonate solution. After washing the basic solution with ether, the aqueous phase was acidified with concentrated hydrochloric acid to provide a white gum. The gum was dissolved in ether, dried (Na2SO4), filtered and concentrated in vacuo to a semi-solid which was titurated with anhydrous ethyl ether and the resultant solid removed by filtration and discarded. Concentration in vacuo provided 18.5 g of the desired product as a gum.

Workup

  1. temperatureThe solution was refluxed for 15 hours
  2. temperaturecooled
  3. extractionextracted with saturated sodium bicarbonate solution
  4. washAfter washing the basic solution with ether
  5. customto provide a white gum
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a semi-solid which
  9. customthe resultant solid removed by filtration
  10. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-9a74d14eb2054fe98708c314c8994c40
Source dataset
uspto-grants-1987_01
Patent number
US04639529

Reaction notes

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