Thioglycolic Acid → HCID 14514919, compound

HRID 1195263Notes

Reaction equation

HRID 1195263 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][C:9]3=O)=[CH:4][C:3]=2[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[SH:23][CH2:24][C:25]([OH:27])=[O:26]>O1CCCC1.C1C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][CH:9]3[S:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[O:2]1

Participants

9

Reactant 4

HCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 117693157,8-Dihydro-2H-naphtho[2,3-d][1,3]dioxol-5(6H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 14514919HCID 14514919, compoundYield 83.3%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 1Naqueous 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.

Workup

  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 1Naqueous 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

Sources & evidence

ORD record
ord-5b9879628723415faa3112b20c89851c
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

Loading…