Octanoic Acid → Octanoic acid, 1-naphthalenyl ester

HRID 1632677Notes

Reaction equation

HRID 1632677 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.CC([O-])=O.[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CCCCCCC>[C:1]([O:10][C:19]1[C:20]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][CH:18]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 379Octanoic AcidHCID 931NaphthaleneHCID 517044Potassium Acetate

Product 1

HCID 107555Octanoic acid, 1-naphthalenyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8900HeptaneSolvent2×

Procedure

The reaction was carried out in a glass reactor furnished with a thermometer, mechanical stirrer, Dean Stark type collector equipped with a reflux condenser and gas and liquid tubes. The reactor was charged with 40 g. of octanoic acid, 10 g. (78 m mols) of naphthalene, 8 g. of heptane, 0.34 g. (1.5 millimols) of Pd(OAc)2 0.45 g (1.5 m mols of Sb(OAc)3 and 0.15 g (1.5 m mols) of KOAc. Dean Stark Collector was filled with heptane. The reaction was carried out at 170° C. with vigorous stirring for 5 hours. GLC analysis showed that 57 m mols (73% yield) of naphthyl octanoate were produced.

Workup

  1. customThe reaction was carried out in a glass reactor
  2. customfurnished with a thermometer, mechanical stirrer, Dean Stark type collector
  3. customequipped with a reflux condenser
  4. additionThe reactor was charged with 40 g
  5. customwas carried out at 170° C.

Sources & evidence

ORD record
ord-03c78aeabe514fffa2d89c59d36b928c
Source dataset
uspto-grants-1984_10
Patent number
US04477385

Reaction notes

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