Methanol → HCID 53905262, compound

HRID 2289107Notes

Reaction equation

HRID 2289107 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].CO>CN(C)C=O.O>[CH:22]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[CH:23][CH3:24]

Participants

7

Reactant 4

HCID 887MethanolHCID 7638MonobenzoneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 53905262HCID 53905262, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5.0 grams (25.0 mmole, 1.0 eq.) of 4-benzyloxyphenol was dissolved in 100 ml of N,N-dimethylformamide. 10.4 grams (75.0 mmole, 3.0 eq.) of potassium carbonate and 3.25 ml (37.5 mmole, 1.5 eq.) of allyl bromide were added to the reaction and it was stirred at 80° C. for 3 hours and at room temperature for another 136 hours. The reaction mixture was diluted with water and extracted 3× with 60 ml of ethyl acetate. The combined organics were dried over sodium sulfate, filtered, evaporated and pumped on high vacuum overnight. The title compound (4.3 grams, 72% yield) was isolated by recrystallization from methanol.

Workup

  1. extractionextracted 3× with 60 ml of ethyl acetate
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custompumped on high vacuum overnight

Sources & evidence

ORD record
ord-7bf25ba9568f4fdabd940e909a9593ca
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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