Sulfuric Acid → chrysanthemic acid d-trans-form

HRID 267571

Reaction equation

HRID 267571 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 80.5%

Procedure

The water layer was made acidic with sulfuric acid and extracted with toluene (80 g) two times. The toluene layer was washed and evaporated, and the residue was distilled under reduced pressure to give trans-chrysanthemic acid (47.1 g; trans-isomer, 80.5 %). B.P. 110° to 114°C/2 mmHg.

Workup

  1. extractionextracted with toluene (80 g) two times
  2. washThe toluene layer was washed
  3. customevaporated
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-3556e4eb9bea4bf1a3c659a1dcdfbbb2
Source dataset
uspto-grants-1976_03
Patent number
US03943167

Linked notes

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