Butanethiol → Chrysanthemic Acid

HRID 1198854Notes

Reaction equation

HRID 1198854 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][C@@H:4]1[C:6]([CH3:8])([CH3:7])[C@@H:5]1[C:9]([OH:11])=[O:10].C(S)CCC>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[C:6]([CH3:7])([CH3:8])[CH:5]1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 8012ButanethiolHCID 3360626771-11-9

Product 1

HCID 2743Chrysanthemic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (+)-cis chrysanthemic acid (1.0 g) in toluene (9 g) was added n-butanethiol (107 mg). Irradiation with a high pressure mercury lamp (100 W) was made for one hour. After the reaction was over, similar after-treatment as in Example 1 was applied to obtain chrysanthemic acid (0.9 g). The optical isomer ratio of the product was (+)-cis, 3.0%; (-)-cis, 2.1%; (+)-trans, 46.6%; and (-)-trans, 48.3%.

Workup

  1. customIrradiation with a high pressure mercury lamp (100 W)

Sources & evidence

ORD record
ord-398147403a344a9eaa82a6033ed33710
Source dataset
uspto-grants-1990_02
Patent number
US04898655

Reaction notes

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