Thioglycolic Acid → HCID 10497178, compound

HRID 609880Notes

Reaction equation

HRID 609880 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[NH2:16][CH2:17][CH2:18][CH2:19][OH:20].[SH:21][CH2:22][C:23](O)=[O:24]>C1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]2[N:16]([CH2:17][CH2:18][CH2:19][OH:20])[C:23](=[O:24])[CH2:22][S:21]2)[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 90863-Amino-1-propanolHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehyde

Product 1

HCID 10497178HCID 10497178, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene (50 ml) were suspended 3,5-diisopropyl-4-hydroxybenzaldehyde (5.00 g) and 3-aminopropanol (1.82 g) in a nitrogen atmosphere. A Dean-Stark trap was fitted to the reactor, and the suspension was refluxed for 1.5 hours. After allowing the mixture to cool, α-mercaptoacetic acid (2.23 g) was added, then the mixture was further refluxed for 2 hours. After removal of benzene by evaporation, water (50 ml) was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 99:1) to afford 1.97 g (24%) of the title compound as a colorless oil. NMR (CDCl3, 60 MHz): 1.23 (12H, d, J=6.6 Hz), 1.0-1.8 (2H, m), 2.5-3.8 (7H, m), 3.73 (2H, brs), 5.50 (2H, brs), 6.92 (2H, s)

Workup

  1. customA Dean-Stark trap was fitted to the reactor
  2. temperaturethe suspension was refluxed for 1.5 hours
  3. temperatureto cool
  4. temperaturethe mixture was further refluxed for 2 hours
  5. customAfter removal of benzene
  6. customby evaporation, water (50 ml)
  7. additionwas added to the residue
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 99:1)

Sources & evidence

ORD record
ord-c50c82ab246240308362489dfb369420
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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