Acetone → HCID 11402885, compound

HRID 742780Notes

Reaction equation

HRID 742780 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:10][C:11]([CH3:13])=O.[CH3:14]S(O)(=O)=O.[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:25][C:19]1[C:24]([CH3:14])=[CH:23][C:22]2[O:9][C:4]3[C:5](=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)[C:11]([CH3:13])([CH3:10])[C:21]=2[CH:20]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 72493,4-Dimethylphenol

Product 1

HCID 11402885HCID 11402885, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 2.126 g (17.4 mmol) of 3,4-dimethylphenol, 98 mg (1.69 mmol) of acetone, and 20.9 mg (0.22 mmol) of methanesulfonic acid was heated for 62 hours at 100° C. and then at 150° C. for 26 hours. The mixture was allowed to cool, diluted with 30 mL of toluene, and washed three times with a 10% aqueous NaOH solution, water and brine. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. There was obtained 335 mg of crude 2,3,6,7,9,9-hexamethylxanthene as a tan solid.

Workup

  1. temperatureto cool
  2. washwashed three times with a 10% aqueous NaOH solution, water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3533bb14c5bb466f822296ec84a69612
Source dataset
uspto-grants-1996_09
Patent number
US05554770

Reaction notes

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