Oxalyl chloride → HCID 15572116, compound

HRID 354626Notes

Reaction equation

HRID 354626 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. Absolute methanol (75 mL) is added to the solid acid chloride. The mixture is stirred magnetically until complete solution is obtained, then refluxed for 45 minutes. The solvent is evaporated in vacuo to give a crystalline solid. The yield of crude ester melting at 83.5°-84.5° C. (uncorr.) is 5.210 g. (99.31%). Recrystallization of this 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. additionAbsolute methanol (75 mL) is added to the solid acid chloride
  8. customis obtained
  9. temperaturerefluxed for 45 minutes
  10. customThe solvent is evaporated in vacuo
  11. customto give a crystalline solid
  12. customRecrystallization of this material from methanol
  13. customaffords colorless rods melting at 86.0°-86.5° C. (uncorr.) in a yield of 3.508 g

Sources & evidence

ORD record
ord-28dcf300a7e04bdfb903367744a49a45
Source dataset
uspto-grants-1983_03
Patent number
US04376124

Reaction notes

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