Potassium Carbonate → HCID 21933594, compound

HRID 1370169Notes

Reaction equation

HRID 1370169 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][C:10]([OH:12])=[O:11].[SH:13][C:14]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>CC(C)=O>[OH:12][C:10]([CH2:9][CH2:8][S:13][C:14]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115533-Bromopropionic acidHCID 1565712452948-12-6

Product 1

HCID 21933594HCID 21933594, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g (0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g (0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone, and the reaction mixture was stirred at room temperature for 12 hours. The solvent was distilled off, the residue was taken up in water and the mixture was extracted with diethyl ether. The aqueous phase was then made acidic using concentrated hydrochloric acid and the precipitate was filtered off with suction and dried. This gave 160 g (88%) of methyl 2-(2-hydroxycarbonyeth-1-yl)thio-4-chlorobenzoate M.p.: 133 to 136° C.

Workup

  1. distillationThe solvent was distilled off
  2. extractionthe mixture was extracted with diethyl ether
  3. filtrationthe precipitate was filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-6eaed12f90fb4c01b1ea2eaed373a234
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

Loading…