p-Toluenesulfonic acid → (4-Methoxy-2-methylphenyl)(4-methoxyphenyl)methanone

HRID 974114Notes

Reaction equation

HRID 974114 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10](Cl)(=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.FC1C=CC=CC=1C(C1C=CC(OC)=C(OC)C=1)=O.C(O)C#C.C1C2C(=CC=CC=2)C=CC=1O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>[Cl-].[Al+3].[Cl-].[Cl-].C1C=CC=CC=1.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][C:7]=1[C:10]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:19]

Participants

11

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 7477p-Anisoyl chlorideHCID 75303-MethoxytolueneHCID 7859Propargyl alcoholHCID 86632-NaphtholHCID 14798Sodium HydroxideHCID 14297443HCID 14297443, compound2×

Product 1

HCID 19905784(4-Methoxy-2-methylphenyl)(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 3

HCID 6451240Aluminum(III) ChlorideCatalystHCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

2-methyl-4,4'-dimethoxybenzophenone was prepared from the Friedel-Crafts reaction of 3-methyl anisole with anisoyl chloride using aluminum chloride as catalyst and hexane as the solvent. The benzophenone product (6.1 grams, 0.02 mole) was converted to the propargyl alcohol according to the procedure of Example 1, Step 2. The resulting crude oil was taken up in 150 milliliters of benzene and 2.8 grams (0.01 mole) of 2-naphthol and 0.1 grams of p-toluene sulfonic acid were added to the benzene solution. The resulting mixture was stirred at room temperature for about 30 minutes and then poured into an equal volume of 5 percent aqueous sodium hydroxide. The organic layer was washed with water and the benzene solvent removed on a rotary evaporator. The remaining crude product was subjected to column chromatography using a 1:1 mixture of chloroform and hexane as elutant. The photochromic fractions were combined and the product crystallized from a mixture of hexane and ether. The product had a melting range of 112-114C. Nuclear Magnetic Resonance (NMR) analysis of the product confirmed it to be, 3(2-methyl-4-methoxyphenyl)-3-(4methoxyphenyl)-3H-naphtho-[2,1-b]pyran.

Workup

  1. washThe organic layer was washed with water
  2. customthe benzene solvent removed on a rotary evaporator
  3. additiona 1:1 mixture of chloroform and hexane as elutant
  4. customthe product crystallized from a mixture of hexane and ether

Sources & evidence

ORD record
ord-fda2eef360d047bb9a3aca7e75cbf3fd
Source dataset
uspto-grants-1991_11
Patent number
US05066818

Reaction notes

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