Sulfuric Acid → chrysanthemic acid d-trans-form

HRID 267573

Reaction equation

HRID 267573 reaction equation
CC[O:3][C:4]([CH:6]1[C:8]([CH3:10])([CH3:9])[CH:7]1[CH:11]=[C:12]([CH3:14])[CH3:13])=[O:5].S(=O)(=O)(O)O>>[CH3:13][C:12]([CH3:14])=[CH:11][C@H:7]1[C:8]([CH3:9])([CH3:10])[C@@H:6]1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 7334Ethyl chrysanthemate

Product 1

HCID 16747chrysanthemic acid d-trans-formYield 80%

Procedure

The water layer was made acidic with sulfuric acid and extracted with toluene (20 g) two times. The toluene layer was washed and distilled under reduced pressure to give trans-chrysanthemic acid (4.2 g; trans-isomer, 80.0 %). B.P. 122° to 130°C/3.3 mmHg.

Workup

  1. extractionextracted with toluene (20 g) two times
  2. washThe toluene layer was washed
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c809d282989e4a5fb9afded6da017da3
Source dataset
uspto-grants-1976_03
Patent number
US03943167

Linked notes

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