Benzhydrol → HCID 18427061, compound

HRID 1279137Notes

Reaction equation

HRID 1279137 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:15]1([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>FC(F)(F)C(O)=O>[C:15]1([CH:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7037BenzhydrolHCID 54350211-Mercaptoundecanoic Acid

Product 1

HCID 18427061HCID 18427061, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 11-mercaptoundecanoic acid (300 mg, 1.3 mmol) and diphenylmethanol (255 mg, 1.3 mmol) in trifluoroacetic acid was stirred at RT, under nitrogen for 30 min. Trifluoroacetic acid was evaporated under high vacuum, the residue dissolved in ether (20 ml), washed with water (3×20 ml), dried and evaporated. The residue was purified by chromatography (light pet—ethyl acetate, 80:20-50:50) on silica to give the desired product (220 mg, 42%), m.p. (Found C, 74.55; H, 8.77. C24H34O2S requires C, 74.96; H, 8.39) ms (EI) 384.

Workup

  1. customTrifluoroacetic acid was evaporated under high vacuum
  2. dissolutionthe residue dissolved in ether (20 ml)
  3. washwashed with water (3×20 ml)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography (light pet—ethyl acetate, 80:20-50:50) on silica

Sources & evidence

ORD record
ord-0a5f7939e3454b6fab7407a506f0aa33
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Reaction notes

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