Thioglycolic Acid → 2-Carboxymethylthio-2-methyltetrahydrofuran

HRID 847340Notes

Reaction equation

HRID 847340 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][CH:6]=1.[SH:7][CH2:8][C:9]([OH:11])=[O:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:1][C:2]1([S:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][O:3]1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 6101p-Toluenesulfonic acidHCID 151452,3-Dihydro-5-methylfuran

Product 1

HCID 199579892-Carboxymethylthio-2-methyltetrahydrofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-4,5-dihydrofuran and 2-mercaptoacetic acid in THF are treated with a catalytic amount of para-toluene sulfonic acid according to the procedure in Example I.A.2. After removal of the solvent, S-(2-methyl-tetrahydrofuran-2-yl) mercaptoacetic acid is obtained. Alternatively, mercaptosuccinic acid is reacted with 2-methyl-4,5-dihydrofuran and then converted to a mercaptosuccinic anhydride derivative by a dehydrating agent such as dicyclohexyl carbodiimide.

Workup

  1. customAfter removal of the solvent

Sources & evidence

ORD record
ord-830539f29cae46b183a8347432d38385
Source dataset
uspto-grants-1992_08
Patent number
US05141648

Reaction notes

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