Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 20035829, compound

HRID 1905546Notes

Reaction equation

HRID 1905546 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:31][CH2:32][Cl:33])(=O)=O)=CC=1>C(C(C)=O)C>[Cl:33][CH2:32][CH2:31][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 20035828116833-86-4

Product 1

HCID 20035829HCID 20035829, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a 20-liter reactor provided with a mechanical stirrer and reflux cooler, 1078 g of methyl 2,3-dihydro-5-hydroxy-1H-inden-1-carboxylate were dissolved with 9 l of dry methyl ethyl ketone, 1162 g of anhydrous potassium carbonate were added and stirred for 30 minutes; then 1448 h of 2-chloroethyl p-toluensulphonate were added and refluxed in oil bath for 50 hours. The mixture was allowed to cool, the insoluble solid was filtered and washed twice with acetone over the same filter. The filtrate was evaporated and dried at vacuum, the residue was dissolved in 4.7 l of toluene and extracted with 1.8 l of 3N sodium hydroxyde solution through the decantation funnel and mechanical stirring for 15 minutes; then it was neutralized with water and dried. After evaporation of solvent at vacuum, the residue as reddish liquid weighed 1419 g (99%). Thin-layer chromatography (silica-gel) showed a major spot and a slight shadow at lower Rf. Cl analysis correct. It was used for the following synthesis step without further purification.

Workup

  1. customIn a 20-liter reactor provided with a mechanical stirrer
  2. additionwere added
  3. temperaturerefluxed in oil bath for 50 hours
  4. temperatureto cool
  5. filtrationthe insoluble solid was filtered
  6. washwashed twice with acetone over the same filter
  7. customThe filtrate was evaporated
  8. customdried at vacuum
  9. dissolutionthe residue was dissolved in 4.7 l of toluene
  10. extractionextracted with 1.8 l of 3N sodium hydroxyde solution through the decantation funnel
  11. stirringmechanical stirring for 15 minutes
  12. customdried
  13. customAfter evaporation of solvent at vacuum
  14. customIt was used for the following synthesis step without further purification

Sources & evidence

ORD record
ord-575b14e1d27f474d87fe8ad3aca8282a
Source dataset
uspto-grants-1989_06
Patent number
US04843165

Reaction notes

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