Water → 2-(3,4-Methylenedioxy-phenoxy)lauric acid ethyl ester

HRID 1590022Notes

Reaction equation

HRID 1590022 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[CH2:11]([O:13][C:14](=[O:27])[CH:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:11]([O:13][C:14](=[O:27])[CH:15]([O:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68289SesamolHCID 95583Ethyl 2-bromododecanoate

Product 1

HCID 544726552-(3,4-Methylenedioxy-phenoxy)lauric acid ethyl esterYield 79.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sesamol (42.7 grams) was dissolved in 300 ml of DMF, 100 grams of 2-bromolauric acid ethyl ester was added and the mixture was stirred. Potassium carbonate (50 grams) was added and the mixture was reacted at 80° C. for 10 hours. The end of the reaction was verified using TLC, after which 1 liter of water and 500 ml of ethyl acetate were added and the mixture was extracted. The organic layer was washed twice with water and then dried over magnesium sulfate and, on removing the solvent by distillation, 90 grams of 2-(3,4-methylenedioxy-phenoxy)lauric acid ethyl ester was obtained as an oily material for a yield of 79.9%.

Workup

  1. customthe mixture was reacted at 80° C. for 10 hours
  2. extractionthe mixture was extracted
  3. washThe organic layer was washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customon removing the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-bf85a3e304ff46e39f3eafa4c5c6339f
Source dataset
uspto-grants-1993_04
Patent number
US05202225

Reaction notes

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