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

HRID 1532159Notes

Reaction equation

HRID 1532159 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-3fece30b28584073b9ad6c37678d9a71
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

Loading…