Myristyl bromide → 7-Tetradecyloxy-4-methyl-coumarin

HRID 903910Notes

Reaction equation

HRID 903910 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O>[CH2:34]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 52805674-Methylumbelliferone

Product 1

HCID 233355707-Tetradecyloxy-4-methyl-coumarinYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

35.2 g (0.2 mole) of 7-hydroxy-4-methyl-coumarin, 27.6 g (0.2 mole) of potassium carbonate, 55.4 g (0.2 mole) of 1-bromotetradecane and 600.0 ml of dry dimethylformamide are stirred in a steam bath overnight. The mixture is cooled and extracted into 1.5 liters of diethyl ether. The ether layer is washed 5 times with saturated saline. It is dried (Na2SO4) and evaporated. The ether is replaced with 800 ml of hexane. The mixture is recrystallized therefrom, yielding 68.3g (92%) of 7-tetradecyloxy-4-methyl-coumarin, m.p. 61°-62° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted into 1.5 liters of diethyl ether
  3. washThe ether layer is washed 5 times with saturated saline
  4. dry with materialIt is dried (Na2SO4)
  5. customevaporated
  6. customThe mixture is recrystallized

Sources & evidence

ORD record
ord-7630d322d6e84d869274d8bc1b9de5a4
Source dataset
uspto-grants-1980_10
Patent number
US04229467

Reaction notes

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