alpha,alpha'-Dichloro-p-xylene → HCID 19779038, compound

HRID 2081932Notes

Reaction equation

HRID 2081932 reaction equation
[C:1]([O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1>C(#N)C>[Cl-:15].[Cl-:15].[C:1]([O:9][CH2:10][CH2:11][N+:12]([CH3:14])([CH3:13])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N+:12]([CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([CH3:13])[CH3:14])=[CH:19][CH:18]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 751582-Dimethylaminoethyl benzoate

Product 1

HCID 19779038HCID 19779038, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 38.64 grams (0.20 mol) of 2-(N,N-dimethylamino)ethyl benzoate prepared as described in Example 1, 17.51 grams (0.10 mol) of α,α'dichloro-p-xylene and 112 milliters of acetonitrile was heated at reflux for 10 minutes. Solid began to precipitate at this time. Acetonitrile (55 milliters) was added and heating was continued for another 5 minutes. The reaction set up to a solid mass and was cooled. The solid was collected with acetonitrile rinse. The solid was washed with ether and dried. The yield of product was 44.0 grams (78.4% of theory); mp=209° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 minutes
  3. customto precipitate at this time
  4. additionAcetonitrile (55 milliters) was added
  5. temperatureheating
  6. temperaturewas cooled
  7. customThe solid was collected with acetonitrile
  8. washrinse
  9. washThe solid was washed with ether
  10. customdried

Sources & evidence

ORD record
ord-43ac44f6c4c74e3c8c3790180abd24ce
Source dataset
uspto-grants-1993_02
Patent number
US05187037

Reaction notes

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