Hydrochloric Acid → 2-(2-Acetoxypropyl)naphthalene

HRID 21357Notes

Reaction equation

HRID 21357 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:11][C:12](=[O:14])[CH3:13])(=O)[CH3:9].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:12]([O:11][CH:8]([CH3:9])[CH2:7][C:1]1[CH:6]=[CH:5][C:4]2[C:3](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:2]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7918Acetic Anhydride

Product 1

HCID 199337452-(2-Acetoxypropyl)naphthalene

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In a four-necked flask equipped with a thermometer and stirrer, were placed 15.1 g (0.08 mole) of the compound (XII-1) obtained in Preparation Example 1, 50 ml of toluene and 20 ml of pyridine, thereafter 10.2 g (0.1 mole) of acetic anhydride and 0.1 g of 4-dimethylaminopyridine was added thereto, and the resulting mixture was stirred at 40°-50° C. for 4 hours. After completion of the reaction, the reaction mixture was poured into 50 ml of 4N hydrochloric acid to conduct extraction and layer separation. The organic layer obtained was washed successively with 1N hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water. The organic layer was then concentrated under reduced pressure to obtain 18.2 g of 2-(2-acetoxypropyl)naphthalene (XIII-1). Yield: 99 0%, nD20 1,5413

Workup

  1. customIn a four-necked flask equipped with a thermometer and stirrer
  2. customAfter completion of the reaction
  3. extractionextraction and layer separation
  4. customThe organic layer obtained
  5. washwas washed successively with 1N hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water
  6. concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-12560695943c426e871f7f672340ce90
Source dataset
uspto-grants-1995_06
Patent number
US05422038

Reaction notes

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