Benzene → HCID 14514901, compound

HRID 2259731Notes

Reaction equation

HRID 2259731 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 of 103 g of 1-(1,3-benzodioxol-5-yl)-1-butanol, 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 h. 2,000 ml of ether was added to the reaction mixture. After washing with water, the product was redissolved in 750 ml of 1N NaOH and then in 100 ml thereof. The solution thus obtained was washed with ether and then with chloroform, acidified with concentrated hydrochloric acid and extracted with 800 ml and then 400 ml of ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 132 g of the crude product. It was purified according to silica gel column chromatography (ethyl acetate/hexane/formic acid=100:900:1) to obtain 127 g of the intended compound in the form of a colorless oil. This oil was crystallized from n-hexane to obtain 115 g of the titled compound as a white crystalline powder. It was found to have a melting point of 59° to 61° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. washAfter washing with water
  4. dissolutionthe product was redissolved in 750 ml of 1N NaOH
  5. customThe solution thus obtained
  6. washwas washed with ether
  7. extractionextracted with 800 ml
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto obtain 132 g of the crude product
  12. customIt was purified

Sources & evidence

ORD record
ord-bb364b20793d45fdb50e821c124fe032
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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