Dimethyl Sulfate → HCID 21277003, compound

HRID 2292213Notes

Reaction equation

HRID 2292213 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:13].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.C(OCC)C.O>CC(=O)CC>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH3:21])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:13]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14421654HCID 14421654, compoundHCID 21584184Diethylether water

Product 1

HCID 21277003HCID 21277003, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of three grams of (2,4-dihydroxy-3-propylphenyl)(2-hydroxyphenyl)methanone in 50 ml of 2-butanone were added 3.04 g of potassium carbonate and 0.52 ml of dimethyl sulfate. The mixture was stirred at reflux temperature overnight, cooled to 25° C., and poured into diethyl ether/water. The layers were separated. The organic layer was washed twice with water, once with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated providing 2.94 g of the desired title product as an oil.

Workup

  1. temperatureat reflux temperature overnight
  2. customThe layers were separated
  3. washThe organic layer was washed twice with water, once with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd8e84d6ed0f4e8086e498e7bedf2d96
Source dataset
uspto-grants-1989_01
Patent number
US04801616

Reaction notes

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