Potassium Carbonate → 92642-95-0

HRID 1660493Notes

Reaction equation

HRID 1660493 reaction equation
Br[CH:2]([CH2:8]Br)[C:3]([O:5]CC)=[O:4].C(=O)([O-])[O-].[K+].[K+].[SH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]>CC(C)=O.C(Cl)Cl>[O:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[S:16][CH2:8][CH:2]1[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 97945Ethyl 2,3-dibromopropionate

Product 1

HCID 1340891892642-95-0

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 41.6 g of ethyl 2,3-dibromopropionate, 400 ml of dry acetone and 11.1 g of potassium carbonate, there was added dropwise at 27° C. a solution of 19.5 g of o-mercaptophenol in 75 ml of acetone. After the addition was complete, the reaction mixture was stirred at room temperature for 10 minutes and an additional 50.9 g of potassium carbonate was added. The reaction mixture then was refluxed for 2 hours, and allowed to stand overnight at room temperature. The mixture was filtered and the solid was washed with acetone, the washings being added to the filtrate. The acetone was stripped to leave a liquid, which was taken up in methylene chloride. The resulting solution was washed with water and dried (MgSO4), and the solvent was stripped. The resulting liquid was dry column chromatographed through silica gel, using a 4:16:80 by volume mixture of tetrahydrofuran, ethyl acetate and hexane (Solvent No. 2) as eluent, to give the ethyl ester of 2,3-dihydro-1,4-benzoxathiin-2-carboxylic acid (1A), as a light yellow liquid, boiling point not determined.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture then was refluxed for 2 hours
  3. waitto stand overnight at room temperature
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with acetone
  6. additionthe washings being added to the filtrate
  7. customto leave a liquid, which
  8. washThe resulting solution was washed with water
  9. dry with materialdried (MgSO4)
  10. customThe resulting liquid was dry column
  11. customchromatographed through silica gel
  12. additionby volume mixture of tetrahydrofuran, ethyl acetate and hexane (Solvent No. 2) as eluent

Sources & evidence

ORD record
ord-e09ce0a7b8094c7582bb5750a909a707
Source dataset
uspto-grants-1981_12
Patent number
US04308276

Reaction notes

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