2-Methylbenzenesulfonic acid → 2-Oxopentyl-o-toluene sulfonate

HRID 648229Notes

Reaction equation

HRID 648229 reaction equation
[N+](=[CH:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7])=[N-].[C:9]1([CH3:19])[C:10]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1>C(Cl)(Cl)Cl>[O:8]=[C:4]([CH2:5][CH2:6][CH3:7])[CH2:3][O:18][S:15]([C:10]1[C:9]([CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 537665711-Diazopentan-2-one

Product 1

HCID 128216102-Oxopentyl-o-toluene sulfonateYield 59.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 1.0 g quantity of 1-diazo-2-pentanone is dissolved in 50 ml of chloroform, and 2.2 g of o-toluenesulfonic acid is slowly added to the solution. The same procedure as in Example 1 is thereafter repeated to afford 1.37 g of 2-oxopentyl-o-toluene sulfonate in the form of a transparent colorless oil (Compound 29).

Sources & evidence

ORD record
ord-560a7401c74a4a5186e5fd8e55586548
Source dataset
uspto-grants-1983_10
Patent number
US04411911

Reaction notes

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