Acetic Acid → HCID 57151048, compound

HRID 2209545Notes

Reaction equation

HRID 2209545 reaction equation
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].Br[C@H:7]([CH3:11])[C:8]([OH:10])=[O:9].O.C(O)(=O)C>CCO>[C:2]([S:5][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6387tert-Butyl mercaptanHCID 6992152(2R)-2-Bromopropanoic acid

Product 1

HCID 57151048HCID 57151048, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 483 mg of Na in 10 mL of EtOH was added 10 mL of tert-butylthiol with stirring at room temperature under nitrogen. After 10 min a solution of 1.53 g of (2R)-2-bromopropanoic acid in 3 mL of EtOH was added and the stirring was continued at room temperature for 3 h. The reaction mixture was poured into water and was acidified with acetic acid and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and was evaporated under water aspirator vacuum using a trap containing bleach to give 1.48 g of (2S)-2-(tert-butylthio)propanoic acid as an oil at 92% yield. Characteristic analytical data are as follows: 1H NMR (300 MHz, CDCl3) δ3.44 (q, J=7 Hz, 1H), 1.49 (d, J=7 Hz, 3H), 1.37 (s, 9H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customwas evaporated under water
  4. additioncontaining bleach

Sources & evidence

ORD record
ord-c6d14cbecff049508155c47bb5dd0e02
Source dataset
uspto-grants-1995_10
Patent number
US05455262

Reaction notes

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