alpha-Naphthaleneacetic acid, ethyl ester → Diethyl 2-(1-naphthyl)malonate

HRID 1613332

Reaction equation

HRID 1613332 reaction equation
[C:1]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:17](=O)([O-:21])[O:18][CH2:19][CH3:20].[O-]CC.[Na+].[Na]>C(O)C>[C:1]1([CH:11]([C:17]([O:18][CH2:19][CH3:20])=[O:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 62428alpha-Naphthaleneacetic acid, ethyl esterHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21226545CID 21226545

Product 1

HCID 240505Diethyl 2-(1-naphthyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 103.9 g (485 mmol) of ethyl naphthalene-1-acetate and 430 ml of ethyl carbonate is stirred at 105° C., and a solution of sodium ethoxide (11 g (478 mmol) of sodium in 255 ml of absolute ethanol) is then added in such a way that the ethanol distils in the course of the introduction. The mixture is heated for a further 15 min. to distil the maximum amount of ethanol, the flask is rapidly cooled and the mixture is poured onto 300 g of crushed ice and 20 ml of concentrated hydrochloric acid. It is extracted with diethyl ether, the organic phase is dried over magnesium sulphate and filtered, and the solvent is evaporated under reduced pressure. An oil is obtained which crystallises in pentane in the cold. The crystals are separated by filtration, treated with vegetable charcoal in diethyl ether and filtered, the filtrate is evaporated and the residue is recrystallised in a 25:75 mixture of diethyl ether/pentane. 97 g (339 mmol) of crystals are obtained.

Workup

  1. customdistils in the course of the introduction
  2. temperatureThe mixture is heated for a further 15 min.
  3. customto distil the maximum amount of ethanol
  4. temperaturethe flask is rapidly cooled
  5. additionthe mixture is poured onto 300 g of crushed ice and 20 ml of concentrated hydrochloric acid
  6. extractionIt is extracted with diethyl ether
  7. dry with materialthe organic phase is dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent is evaporated under reduced pressure
  10. customAn oil is obtained which
  11. customcrystallises in pentane in the cold
  12. customThe crystals are separated by filtration
  13. additiontreated with vegetable charcoal in diethyl ether
  14. filtrationfiltered
  15. customthe filtrate is evaporated
  16. customthe residue is recrystallised in a 25:75 mixture of diethyl ether/pentane

Sources & evidence

ORD record
ord-46828f382bbf4f77a27019604f3708f7
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Linked notes

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