Acetyl chloride → 2-(Acetyloxy)-4-(methylsulfanyl)butanoic acid

Reaction equation

[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O-:5])=[O:4].[Ca+2].[OH:11][CH:12](CCSC)[C:13]([O-])=O.C(Cl)(=O)C>>[C:12]([O:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4])(=[O:11])[CH3:13]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 107344Calcium bis(2-hydroxy-4-(methylthio)butyrate)

Product 1

HCID 30747282-(Acetyloxy)-4-(methylsulfanyl)butanoic acidYield 192.7%

Procedure

Calcium 2-hydroxy-4-(methylthio)butyrate (33.8 g, 0.1 g-mole) and acetyl chloride (110 g) are refluxed in a 250 ml round-bottom flask for 2.5 hours. The mixture is evaporated to a syrup and treated with 150 ml acetone. The brown mixture is stirred for 30 minutes, filtered, and the filtrate evaporated to dryness to give 37 g, 96.4% of brown viscous oil which is identified by TLC and nmr.

Workup

customThe mixture is evaporated to a syrup
additiontreated with 150 ml acetone
filtrationfiltered
customthe filtrate evaporated to dryness

Sources & evidence

ORD record: ord-8174378126114fb7810c69dbc4a7ccd9
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075502

Reaction notes

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