p-Toluenesulfonic acid monohydrate → HCID 12095194, compound

HRID 434202Notes

Reaction equation

HRID 434202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([C:13]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[O:21][CH3:22])O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[C:38]=1[CH2:45][C:46]1[C:51]([O:52][CH3:53])=[CH:50][CH:49]=[CH:48][C:47]=1[O:54][CH3:55]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([C:13]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[O:21][CH3:22])[CH:45]([C:38]1[C:39]([O:43][CH3:44])=[CH:40][CH:41]=[CH:42][C:37]=1[O:36][CH3:35])[C:46]1[C:51]([O:52][CH3:53])=[CH:50][CH:49]=[CH:48][C:47]=1[O:54][CH3:55]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 10979619HCID 10979619, compoundHCID 12095193HCID 12095193, compound

Product 1

HCID 12095194HCID 12095194, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of bis(2,6-dimethoxyphenyl)methanol (1.52 g, 0.005 mol) in acetonitrile (50 mL) at room temperature was added p-toluenesulfonic acid monohydrate (0.95 g, 0.005 mol). To the resulting deep red solution was added bis(2,6-dimethoxyphenyl)methane (1.44 g, 0.005 mol). The reaction mixture decolored within about one hour and was stirred for an additional 17 hours. The reaction was quenched by the addition of water (10 mL), extracted with dichloromethane and dried over anhydrous magnesium sulfate. Evaporation of the solvent and hot filtration using hexane/benzene gave 1,1,2,2-tetrakis(2′,6′-dimethoxyphenyl)ethane as a mixture of rotational isomers after evaporation of the solvents and washing with diethyl ether.

Workup

  1. customThe reaction was quenched by the addition of water (10 mL)
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent and hot filtration

Sources & evidence

ORD record
ord-756aab1e61684272aaaa90cc69c485c8
Source dataset
uspto-grants-2003_12
Patent number
US06670512B2

Reaction notes

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