3-Chloro-2-methyl-1-propene → HCID 14795412, compound

HRID 330323Notes

Reaction equation

HRID 330323 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25]([CH3:27])=[CH2:26]>CS(C)=O>[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:26][C:25]([CH3:27])=[CH2:24])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 14795412HCID 14795412, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 14.6 grams (0.0682 mole) of 4,4'-dihydroxybenzophenone and 10.4 grams (0.0751 mole) of potassium carbonate in 250 mL of dimethyl sulfoxide was stirred under a nitrogen atmosphere for 20 minutes. To this was added during a 20 minute period via syringe 7.32 mL (0.0751 mole) of 3-chloro-2-methylpropene. Upon completion of addition the reaction mixture was heated at 60°-65° C. for 18 hours. The reaction mixture was poured into 600 mL of ice-water and then was extracted with four portions of diethyl ether. The combined ether extracts were washed with two 200 mL portions of aqueous 1N sodium hydroxide. The combined sodium hydroxide washes were made acidic with aqueous 20% hydrochloric acid. The resultant solid was dissolved in diethyl ether, and the solution was washed first with a saturated aqueous sodium chloride solution and then with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 8.6 grams of 4-hydroxy-4'-(2-methyl-2-propenoxy)benzophenone.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas heated at 60°-65° C. for 18 hours
  3. extractionwas extracted with four portions of diethyl ether
  4. washThe combined ether extracts were washed with two 200 mL portions of aqueous 1N sodium hydroxide
  5. dissolutionThe resultant solid was dissolved in diethyl ether
  6. washthe solution was washed first with a saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fa328443f9c49c8b9d183c8639c691d
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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