Benzene → HCID 14514901, compound

HRID 2259780Notes

Reaction equation

HRID 2259780 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10](O)[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[SH:15][CH2:16][C:17]([OH:19])=[O:18].C1C=CC=CC=1>CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.CCOCC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 241BenzeneHCID 1133Thioglycolic AcidHCID 10375365HCID 10375365, compound

Product 1

HCID 14514901HCID 14514901, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 103 g of 1-(1,3-benzodioxol-5-yl)-1butanol, 73.3 g of mercaptoacetic acid, 0.1 g of D-10-camphorsulfonic acid and 500 ml of benzene was heated under reflux for 2 hours, followed by the addition of 2000 ml of ether. The obtained mixture was washed with water and extracted with 750 ml and then 100 ml of 1 N sodium hydroxide successively. The extracts were combined, washed with ether and chloroform successively, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (800 ml and 400 ml). The extracts were combined, washed with water, dried over magnesium sulfate and concentrated in a vacuum to obtain 132 g of a crude product. This crude product was purified by silica gel chromatography (ethyl acetate/hexane/formic acid =100:900:1) to obtain 127 g of a colorless oil. This oil was crystallized from n-hexane to obtain 115 g of the title compound as a white crystalline powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. washThe obtained mixture was washed with water
  4. extractionextracted with 750 ml
  5. washwashed with ether and chloroform successively
  6. extractionextracted with ethyl acetate (800 ml and 400 ml)
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in a vacuum
  10. customto obtain 132 g of a crude product
  11. customThis crude product was purified by silica gel chromatography (ethyl acetate/hexane/formic acid =100:900:1)

Sources & evidence

ORD record
ord-44755ad88451450484795d6580fcdf27
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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