Water → HCID 178526172, compound

HRID 230764

Reaction equation

HRID 230764 reaction equation
[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](O)(=O)[CH2:16][SH:17].[OH2:20]>FC(F)(F)C(O)=O>[CH:1]([CH2:15][C:16]([OH:20])=[S:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1133Thioglycolic AcidHCID 7037Benzhydrol

Product 1

HCID 178526172HCID 178526172, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of benzhydrol (100 g, 0.542 mol) in trifluoroacetic acid (300 mL) at room temperature (about 22 degrees C.) was added thioglycolic acid (50 g, 0.542 mol) drop wise over 20 minutes. Reaction progress was monitored by thin layer chromatography (TLC). The reaction was complete within one hour at which point water (1000 mL) was added slowly into the reaction mixture causing the product to precipitate. The resulting precipitate was filtered, washed with water and dried overnight under high vacuum to give benzhydrylthioacetic acid (139.3 g, 99.3%) as a pale yellow solid. (See Prisinzano, T. et al, Tetrahedron Asymm., 2004, 15, 1053-1058)

Workup

  1. customReaction progress
  2. additionwas added slowly into the reaction mixture
  3. customto precipitate
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-09f72cf37365468fb9942dd777925bc3
Source dataset
uspto-grants-2009_07
Patent number
US07566805B2

Linked notes

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