Thioglycolic Acid → HCID 12056532, compound

HRID 277658Notes

Reaction equation

HRID 277658 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[SH:12][CH2:13][C:14]([OH:16])=[O:15].C(OCC)(=O)C>O1CCCC1.N1CCCC1>[N+:1]([CH2:4][CH:5]([S:12][CH2:13][C:14]([OH:16])=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 7626Beta-NitrostyreneHCID 8857Ethyl Acetate

Product 1

HCID 12056532HCID 12056532, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 31268PyrrolidineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of nitrostyrene (10 g, 0.067 mol) in tetrahydrofuran (250 ml) is treated with mercaptoacetic acid (7.4 g, 5.6 ml, 0.08 mol) followed by pyrollidine (3 drops). After stirring for 2 hours the reaction mixture is concentrated onto silica gel and chromatographed, eluting with 4:1, hexanes:ethyl acetate, to give the title product as a solid (13.14 g, 81% yield). Analysis: C8H7NO2. Calculated: C, 49.78; H, 4.60; N, 5.81%. Found: C, 49.50; H, 4.66; N, 5.81%.

Workup

  1. concentrationis concentrated onto silica gel
  2. customchromatographed
  3. washeluting with 4:1, hexanes

Sources & evidence

ORD record
ord-047e204af56d4b01a8f2ef10d434f821
Source dataset
uspto-grants-2002_03
Patent number
US06358883B1

Reaction notes

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