1,3-Benzodioxole → 4-(6-Methoxyhexanoyl)-1,2-methylenedioxybenzene

HRID 2254329Notes

Reaction equation

HRID 2254329 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](O)=[O:9].ClC(Cl)C(OC(=O)C(Cl)Cl)=O.[CH2:22]1[O:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:23]1>ClC(Cl)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:27]1[CH:28]=[CH:29][C:24]2[O:23][CH2:22][O:30][C:25]=2[CH:26]=1)=[O:9]

Participants

5

Reactant 3

HCID 92291,3-BenzodioxoleHCID 77772Acetic acid, 2,2-dichloro-, 1,1'-anhydrideHCID 150030106-Methoxyhexanoic acid

Product 1

HCID 197452284-(6-Methoxyhexanoyl)-1,2-methylenedioxybenzeneYield 89.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

In 50 ml of dichloroethane were dissolved 7.31 g (0.05 mole) of 6-methoxy hexanoic acid and 14.39 g (0.06 mole) of dichloroacetic anhydride. To the resulting solution were added 7.93 g (0.065 mole) of methylenedioxybenzene and 0.71 g of boron trifluoridediethyl ether complex and the resulting mixture was then stirred at 70° C. for 6 hours. After completion of the reaction, the reaction solution was cooled and washed with 5% aqueous sodium carbonate solution and water in this order. The organic layer was concentrated under reduced pressure to obtain 11.2 g of 4-(6-methoxyhexanoyl)-1,2-methylenedioxybenzene.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed with 5% aqueous sodium carbonate solution and water in this order
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bfb6ebd466954ec98ef724551b776de1
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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