Thioglycolic Acid → HCID 14514919, compound

1.2 g of 6,7-methylenedioxy-1-tetralone was added to a suspension of 0.2 g of lithium aluminum hydride in 20 ml of tetrahydrofuran under cooling with ice. The mixture was stirred at room temperature overnight and cooled with ice/water. 0.2 ml of water, then 0.2 ml of a 15% aqueous sodium hydroxide solution and finally 0.6 ml of water were added thereto. Insoluble substances were removed by filtration. The filtrate was concentrated to obtain a crystalline residue. 1.1 g of mercaptoacetic acid and a catalytic amount of D-10-camphosulfonic acid were added to the residue and the mixture was heated in 30 ml of benzene under reflux for 1 h. The reaction mixture was washed with water. After extraction with a 1N aqueous sodium hydroxide solution, the aqueous layer was acidified with 1N hydrochloric acid. After extraction with chloroform, the extract was dried over magnesium sulfate and the solvent was distilled off. The crystalline residue thus obtained was treated according to silica gel column chromatography (chloroform) to obtain 1.4 g of the intended compound in the form of white crystals.

1. temperatureunder cooling with ice
2. customInsoluble substances were removed by filtration
3. concentrationThe filtrate was concentrated
4. customto obtain a crystalline residue
5. temperatureunder reflux for 1 h
6. washThe reaction mixture was washed with water
7. extractionAfter extraction with a 1N aqueous sodium hydroxide solution
8. extractionAfter extraction with chloroform
9. dry with materialthe extract was dried over magnesium sulfate
10. distillationthe solvent was distilled off
11. customThe crystalline residue thus obtained
12. additionwas treated

ORD record

ord-0907b939597440dfa441c4056f31937f

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05475024