Thioglycolic Acid → HCID 13176140, compound

HRID 978623Notes

Reaction equation

HRID 978623 reaction equation
C(N(CC)CC)C.[SH:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:13]([CH:16]1[C:20](O)([CH3:21])[CH:19]=[CH:18][C:17]1=[O:23])[CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[CH2:13]([C:16]1[C:17](=[O:23])[CH2:18][CH:19]([S:8][CH2:9][C:10]([OH:12])=[O:11])[C:20]=1[CH3:21])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13176140HCID 13176140, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into the same flask as used in Example 1, triethylamine (10 g), mercaptoacetic acid (30 g) and toluene (50 g) were charged, and 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (15.2 g) was dropwise added thereto at a temperature of 20° to 40° for 1 hour. Thereafter, the reaction mixture was stirred at a temperature of 50° to 70° C. for 4 hours. After completion of the reaction, the mixture was evaporated under reduced pressure. The residue was dissolved in a 5% aqueous solution of sodium bicarbonate (100 g), and undissolved materials were filtered off. The filtrate was treated with an acid and extracted with diethyl ether. Diethyl ether was evaporated off from the organic layer to obtain 2-allyl-3-methyl-4-carboxymethylthio-2-cyclopentenone (20.5 g). Yield, 90.5%. nD20 1.5567.

Workup

  1. additionwere charged
  2. customAfter completion of the reaction
  3. customthe mixture was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in a 5% aqueous solution of sodium bicarbonate (100 g), and undissolved materials
  5. filtrationwere filtered off
  6. additionThe filtrate was treated with an acid
  7. extractionextracted with diethyl ether
  8. customDiethyl ether was evaporated off from the organic layer

Sources & evidence

ORD record
ord-031164763acb4af98ee7e4a90e1fb77e
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

Loading…