Thioglycolic Acid → HCID 178526172, compound

HRID 230766Notes

Reaction equation

HRID 230766 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.F[C:16](F)(F)[C:17]([OH:19])=O.C(O)(=O)C[SH:24]>ClCCl>[CH:1]([CH2:16][C:17]([OH:19])=[S:24])([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 1133Thioglycolic AcidHCID 6422Trifluoroacetic acidHCID 7037Benzhydrol

Product 1

HCID 178526172HCID 178526172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydrol (90 g, 0.488 mol) and trifluoroacetic acid (90 mL) in dichloromethane (300 mL) was added thioglycolic acid (40 g, 0.488 mol) in dichloromethane (60 mL) drop wise over 20 minutes. The reaction was completed in one hour. The solvent was removed in vacuo to give a crude solid, which was dried overnight under high vacuum. The solid was treated with 2 N NaOH (1.0 L) and washed with t-butylmethylether (200 ml) to remove non carboxylic acid impurities. The aqueous solution was then acidified with concentrated HCl and the resulting precipitate was collected, washed with water and dried to give benzhydrylthioacetic acid (128.5 g) as a colorless solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a crude solid, which
  3. customwas dried overnight under high vacuum
  4. additionThe solid was treated with 2 N NaOH (1.0 L)
  5. washwashed with t-butylmethylether (200 ml)
  6. customto remove non carboxylic acid impurities
  7. customthe resulting precipitate was collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-637f7a0a752a43a682c599ea0baa7cff
Source dataset
uspto-grants-2009_07
Patent number
US07566805B2

Reaction notes

Loading…