Methanesulfonic Acid → HCID 18915766, compound

HRID 1292586Notes

Reaction equation

HRID 1292586 reaction equation
[CH3:1][C:2](=[CH:4][CH3:5])[CH3:3].[OH:6][C:7]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[OH:6][C:7]1[CH:20]=[C:19]([OH:21])[C:18]([C:2]([CH3:3])([CH3:1])[CH2:4][CH3:5])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 85722,4-DihydroxybenzophenoneHCID 105532-Methyl-2-buteneHCID 516892Sodium Bicarbonate

Product 1

HCID 18915766HCID 18915766, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

42 g (0.6 mol) of 2-methyl-2-butene are added dropwise to a solution of 45 g (0.21 mol) of 2,4-dihydroxybenzophenone and 6.1 g (63 mmol) of methanesulfonic acid in 90 ml of toluene and the mixture is held at 75° C. with stirring for 6 h. The reaction mixture is cooled, then treated with 100 ml of NaHCO3 and extracted with ethyl acetate. The resulting solution is washed with water and then with saturated sodium chloride solution. The residue which remains after drying over MgSO4, filtering and concentrating by evaporation is recrystallized from CH2Cl2 /hexane. 53.6 g (89.9%) of 2,4-dihydroxy-5-(1,1-dimethylpropyl)benzophenone are obtained as beige crystals having a melting point of 100°-104° C.

Workup

  1. customis held at 75° C.
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. washThe resulting solution is washed with water
  5. dry with materialafter drying over MgSO4
  6. filtrationfiltering
  7. concentrationconcentrating by evaporation
  8. customis recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-eeef290081e44e26955964143881f54a
Source dataset
uspto-grants-1998_05
Patent number
US05756793

Reaction notes

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