Diazomethane → 1-Diazonio-4-phenylbut-1-en-2-olate

HRID 2185045Notes

Reaction equation

HRID 2185045 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:12](=[CH2:14])=[N-:13]>C(O)(=O)C>[N+:12](=[CH:14][C:1](=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[N-:13]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 64801Benzenepropanoyl chloride

Product 1

HCID 541450391-Diazonio-4-phenylbut-1-en-2-olate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of hydrocinnamoyl chloride (10.00 grams; 100 mL dry diethyl ether) was carefully added to freshly prepared etherial diazomethane (85.6 grams Diazald; 100 mL dry ethyl ether) at 0° C. The reaction was held at 0° C. until outgassing subsided (15 minutes), then raised to room temperature (15 minutes). Acetic acid (5.0 mL) was added and the reaction partitioned (pH4 pthalate buffer and methyl tert-butyl ether). The organic was washed with water, dried over MgSO4 and filtered to provide, upon evaporation, an oil containing the title compound. The crude product was used with no further purification or delay.

Workup

  1. customwas held at 0° C. until outgassing
  2. custom(15 minutes)
  3. customthe reaction partitioned (pH4 pthalate buffer and methyl tert-butyl ether)
  4. washThe organic was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto provide, upon evaporation

Sources & evidence

ORD record
ord-53c210e0dd5743c9834e6169ae235ee1
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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