Benzene → HCID 14514923, compound

HRID 2259784Notes

Reaction equation

HRID 2259784 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10](O)[CH:11]([CH3:13])[CH3:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[SH:15][CH2:16][C:17]([OH:19])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH:11]([CH3:13])[CH3:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1133Thioglycolic AcidHCID 6101p-Toluenesulfonic acidHCID 3469637228-18-4

Product 1

HCID 14514923HCID 14514923, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 2 g of 1-(1,3-benzodioxol-5-yl)-2-methyl-1-propanol, 1.3 g of mercaptoacetic acid, a catalytic amount of p-toluenesulfonic acid and 50 ml of benzene was heated under reflux for 5.5 hours, followed by the addition of ethyl acetate. The mixture was washed with water and extracted with a 2N aqueous solution of sodium hydroxide. The aqueous layer was washed with chloroform, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in a vacuum to obtain a residue. This residue was purified by silica gel column chromatography (chloroform/methanol=20:1) to obtain 2.14 g of the title compound as a colorless oil.

Workup

  1. temperatureunder reflux for 5.5 hours
  2. washThe mixture was washed with water
  3. extractionextracted with a 2N aqueous solution of sodium hydroxide
  4. washThe aqueous layer was washed with chloroform
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customto obtain a residue
  10. customThis residue was purified by silica gel column chromatography (chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-25a7d72f8bc14d3ca44a31204bc079a0
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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