Oxalyl chloride → HCID 15572116, compound

HRID 2286523Notes

Reaction equation

HRID 2286523 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH:7]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[C:12](=[CH:22][C:23]([OH:25])=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1>C1C=CC=CC=1>[CH3:1][O:24][C:23](=[O:25])[CH:22]=[C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:17]=2[CH:16]=[CH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 165241Wy 41770

Product 1

HCID 15572116HCID 15572116, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Oxalyl chloride (2.665 g., 1.79 ml., 0.021 mole) is added to a suspension of (5H-dibenzo[a,d]cyclohepten-5-ylidene)acetic acid (5.000 g., 0.020 mole) in dry benzene (70 ml.). An exothermic reaction occurs and the solid gradually dissolves. After solution is complete, the mixture is refluxed for one hour, then concentrated in vacuo to give an amber oil which crystallizes on storage at ambient temperature. The yield of crude ester melting at 83.5°-84.5° C. (uncorr.) is 5.210 g. (99.31%). Recrystallization of the material from methanol affords colorless rods melting at 86.0°-86.5° C. (uncorr.) in a yield of 3.508 g. (66.86%).

Workup

  1. customAn exothermic reaction
  2. dissolutionthe solid gradually dissolves
  3. temperaturethe mixture is refluxed for one hour
  4. concentrationconcentrated in vacuo
  5. customto give an amber oil which
  6. customcrystallizes on storage at ambient temperature
  7. customRecrystallization of the material from methanol
  8. customaffords colorless rods melting at 86.0°-86.5° C. (uncorr.) in a yield of 3.508 g

Sources & evidence

ORD record
ord-928b840a1cd14fdc9bc8d0011f3731e0
Source dataset
uspto-grants-1981_05
Patent number
US04267192

Reaction notes

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