Hydrochloric Acid → HCID 21397571, compound

HRID 1439423Notes

Reaction equation

HRID 1439423 reaction equation
[Cl:1][C:2]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1)=[O:3].C=O.Cl.[CH:16](Cl)(Cl)[Cl:17]>[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]([O:4][C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[C:9]([CH3:11])[C:10]=1[CH2:16][Cl:17])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 6212ChloroformHCID 220261893,5-Xylyl chloroformate

Product 1

HCID 21397571HCID 21397571, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Into a stirred mixture of 37 parts of 3,5-xylenyl chloroformate, 78 parts of paraformaldehyde, 10 parts of powdered anhydrous zinc chloride, and 150 parts of chloroform at 20-30 degrees, was passed hydrogen chloride gas over 101/2 hours. The paraformaldehyde slowly dissolved. Then the reaction mixture was agitated briefly with ice water, after which the organic layer was decanted, dried over magnesium sulfate, filtered, and solvent was evaporated off. The residual liquid was distilled to obtain 17 parts of chloromethyl-3,5-dimethylphenyl chloroformate, boiling point 80° - 85° (0.005 millimeter), in which the position of the chloromethyl group is indicated to be mostly para by NMR analysis.

Workup

  1. custom2 hours
  2. customafter which the organic layer was decanted
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent was evaporated off
  6. distillationThe residual liquid was distilled

Sources & evidence

ORD record
ord-146e2f64cda94060aae8b9cd36ec8941
Source dataset
uspto-grants-1977_11
Patent number
US04059615

Reaction notes

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