Butyric Acid → 1'-Butyronaphthone

HRID 2254334Notes

Reaction equation

HRID 2254334 reaction equation
[C:1](O)(=[O:5])[CH2:2][CH2:3][CH3:4].ClCC(OC(=O)CCl)=O.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>ClCC(Cl)(Cl)Cl>[C:1]([C:24]1[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][CH:23]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 931NaphthaleneHCID 10946Chloroacetic anhydride

Product 1

HCID 178901'-ButyronaphthoneYield 43%

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Conditions

Temperature
115 °C

Procedure

In 50 ml of tetrachloroethane were dissolved 4.41 g (0.05 mole) of butyric acid and 9.83 g (0.0575 mole) of monochloroacetic anhydride. To the resulting solution were added 7.69 g (0.06 mole) of naphthalene and 0.9 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 115° C. for 8 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 4.26 g of butyrylnaphthalene.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06bad3aebd5742c5a6add243fd3eab61
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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