Hydrochloric Acid → 3-(4-Biphenylylthio)-2-hydroxypropionic acid

HRID 1706411Notes

Reaction equation

HRID 1706411 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([S:7][CH2:8][CH:9]([OH:15])[C:10]([O:12]CC)=[O:11])=[CH:3][CH:2]=1.O.O1CCCC1.Cl>[OH-].[Na+]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][C:4]([S:7][CH2:8][CH:9]([OH:15])[C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 23332067Ethyl 3-(4-biphenylylthio)lactate

Product 1

HCID 233320623-(4-Biphenylylthio)-2-hydroxypropionic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 3-(4-biphenylylthio)lactate (0.093 g, 0.31 mmole), in NaOH (0.5 ml), water (2 ml) and tetrahydrofuran (1 ml) was stirred overnight at 25° C. The mixture was acidified (1 N HCl, 0.5 ml) and then extracted with methylene chloride (3×5 ml). The residue from evaporation of the methylene chloride was recrystallized from acetonitrile to yield 0.065 g of 3-(4-biphenylylthio)-2-hydroxypropionic acid, m.p. 175.5°-176° C.

Workup

  1. extractionextracted with methylene chloride (3×5 ml)
  2. customThe residue from evaporation of the methylene chloride
  3. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5cfa6b5df8ba4577928c2f41c0930f44
Source dataset
uspto-grants-1980_06
Patent number
US04207329

Reaction notes

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