4-Toluenesulfonyl chloride → HCID 12735323, compound

HRID 1614009

Reaction equation

HRID 1614009 reaction equation
[OH-:1].[K+].[C:3]1([CH:9]([OH:18])[CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>CCOCC>[C:25]1([CH3:26])[CH:27]=[CH:28][C:22]([S:19]([O:18][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:10]([O:11][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:20])=[O:1])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 95447Hydrobenzoin

Product 1

HCID 12735323HCID 12735323, compoundYield 412.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium hydroxide (400 mg, 7.0 mmole) was added to a solution of 1,2-diphenylethane-l,2-diol (I40 mg, 0.65 mmole) in dry ether (30 mL). TsCl (286 mg, 1.5 mmole) was added. The reaction was completed after 1 hour with stirring under N2 atmosphere at RT. A white solid was obtained. The white solid was filtered and washed with dichloromethane. The combined filtrate was concentrated, Recrystallization with methylene chloride and hexane gave the crystalline solid (1.4 g, 44.6%), mp, 110-112 (decomposed), 'H-NMR(CDCl3) δ, 2.39(s, 6H CH3), 5.61(s, 2H, CH), 6.89-7.55(m, 18H, ArH).

Workup

  1. customA white solid was obtained
  2. filtrationThe white solid was filtered
  3. washwashed with dichloromethane
  4. concentrationThe combined filtrate was concentrated
  5. customRecrystallization with methylene chloride and hexane

Sources & evidence

ORD record
ord-3c319cfc1762498f9802c93a6ad54e50
Source dataset
uspto-grants-1993_03
Patent number
US05194651

Linked notes

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