Dimethyl Sulfoxide → HCID 54384141, compound

HRID 1110087Notes

Reaction equation

HRID 1110087 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[CH2:19](I)[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CC(=O)CC.CCOCC>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:21][CH:20]=[CH2:19])=[CH:13][CH:12]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 53849917HCID 53849917, compound

Product 1

HCID 54384141HCID 54384141, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-(4-hydroxyphenoxy)benzoic acid methyl ester (5.00 g, 20.5 retool), allyl iodide (3.79 g, 22.5 mmol), potassium carbonate (8.49 g, 61.5 mmol), and dimethylsulfoxide (10 mL) in 2-butanone (40 mL) was refluxed for 24 hours. The mixture was cooled to room temperature and diluted with ether. The resulting mixture was washed once with water and once with saturated sodium bicarbonate solution. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo to provide 4.52 g (78%) of the title intermediate as a white solid: mp 75° C.; 1H--NMR (CDCl3) 7.99 (d, J=9 Hz, 2H), 7.03 (d, J=9 Hz, 2H), 6.95 (m, 4H), 6.08 (m, 1H), 5.46 (d, J=14 Hz, 1H), 5.31 (d, J=10 Hz, 1H), 4.55 (d, J=7 Hz, 2H), 3.92 (s, 3H).

Workup

  1. temperaturewas refluxed for 24 hours
  2. washThe resulting mixture was washed once with water and once with saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1389261371042e98a86dc3175d092f1
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

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