Reaction equation
[Na].[Br:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]([S:9][CH2:13][CH2:12][CH2:11][C:10]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
3.74 g of sodium were dissolved in 77 ml of absolute ethanol under argon. The solution was treated dropwise with 25 g of m-bromothiophenol and heated to reflux. Thereafter, 12.4 ml of γ-butyrolactone were added and the reaction mixture was heated to 110° C. for 5 hours. The separated carboxylic acid sodium salt was removed by filtration, washed with a small amount of ether and dissolved in 300 ml of water. The solution was acidified to pH 2 with 1N HCl while cooling with ice, the free carboxylic acid was extracted with ether, the ethereal solution was dried and evaporated. There were obtained 33.1 g of 4-(m-bromophenylmercapto)butyric acid.
Workup
- temperatureheated to reflux
- customThe separated carboxylic acid sodium salt was removed by filtration
- washwashed with a small amount of ether
- dissolutiondissolved in 300 ml of water
- temperaturewhile cooling with ice
- extractionthe free carboxylic acid was extracted with ether
- customthe ethereal solution was dried
- customevaporated
Sources & evidence
- ORD record
- ord-6cb72450fdfa4b8d8d6fea27607b02ae
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420273
Linked notes
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