3-Bromopropionic acid → 3-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

HRID 378807Notes

Reaction equation

HRID 378807 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[SH:11].Br[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[S:11][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 115533-Bromopropionic acidHCID 14798Sodium HydroxideHCID 776152,5-Xylenethiol

Product 1

HCID 167883143-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

90 g (2.25 mol) of sodium hydroxide were dissolved in 500 ml of water and, with cooling at 10° C., admixed with 147.59 g of 2,5-dimethylthiophenol. Cooling was continued and 180.1 g (1.18 mol) of 3-bromopropionic acid were added below 25° C. The mixture was stirred for another 4 h at room temperature and then washed with diethyl ether (3×500 ml). The aqueous solution was made acidic using 1M HCl, and the precipitated product was filtered off and washed with water.

Workup

  1. temperatureCooling
  2. washwashed with diethyl ether (3×500 ml)
  3. filtrationthe precipitated product was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-a6381f356a23444b9c61ffa6e2b89451
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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