4-Toluenesulfonyl chloride → HCID 54412277, compound

HRID 393138Notes

Reaction equation

HRID 393138 reaction equation
[OH:1][N:2]=[C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:1][N:2]=[C:3]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 73991147HCID 73991147, compound

Product 1

HCID 54412277HCID 54412277, compoundYield 80%

Procedure

18.0 g (0.0722 mol) of hexyl α-(hydroxyimino)-2-phenylacetate are reacted with 15.1 g of p-toluenesulfonic acid chloride as described in example 1.3 to give 23.2 g (80%) of hexyl α-(4-methylphenylsulfonyloxyimino)-2-phenylacetate as a colorless liquid after purification by chromatography. According to 1H-NMR-analysis, the product is a mixture of 69% of the trans isomer and 31% of the cis isomer.

Sources & evidence

ORD record
ord-2cff07df272d4195bcc07b1e1c2ccf26
Source dataset
uspto-grants-2004_10
Patent number
US06806024B1

Reaction notes

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