Ethyl chloroacetate → HCID 21289481, compound

HRID 868010Notes

Reaction equation

HRID 868010 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]1=2.ClC[C:19](OCC)=[O:20].CC(C)([O-])C.[K+].[Na]>C(O)C.C(OCC)C.O.C(O)(C)(C)C>[CH:19]([CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]1=2)=[O:20]

Participants

9

Reactant 4

HCID 7751Ethyl chloroacetateHCID 5360545SodiumHCID 13607596Ethyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21289481HCID 21289481, compoundYield 44.5%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

7.6 g of ethyl 5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was mixed with 6.4 g of ethyl chloroacetate. The mixture was cooled to 5°-10° C. and then a mixture of 5.9 g of potassium tertiary butoxide and 65 ml of tertiary butanol was added thereto over a period of 1 hour. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo at a temperature not more than 30° C. The residue was extracted with diethyl ether and the extract was washed with water, dried and then concentrated in vacuo to give an oily product. The product was dissolved in 25 ml of ethanol. A solution of 0.58 g of sodium in 25 ml of ethanol, and 0.43 ml of water were added successively to the solution. The mixture was stirred at room temperature for 4 hours. Diethyl ether was added to the reaction mixture and the precipitate formed was collected by filtration. The precipitate was mixed with 10 ml of acetic acid and the mixture was heated at 100° C. for 15 minutes. After cooling, water was added to the reaction mixture and the mixture was extracted with diethyl ether. The extract was washed with water, dried and then concentrated in vacuo to give 3.6 g of ethyl 5-formyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate as an oil.

Workup

  1. temperatureThe mixture was cooled to 5°-10° C.
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated in vacuo at a temperature not more than 30° C
  4. extractionThe residue was extracted with diethyl ether
  5. washthe extract was washed with water
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto give an oily product
  9. stirringThe mixture was stirred at room temperature for 4 hours
  10. customthe precipitate formed
  11. filtrationwas collected by filtration
  12. additionThe precipitate was mixed with 10 ml of acetic acid
  13. temperaturethe mixture was heated at 100° C. for 15 minutes
  14. temperatureAfter cooling
  15. additionwater was added to the reaction mixture
  16. extractionthe mixture was extracted with diethyl ether
  17. washThe extract was washed with water
  18. customdried
  19. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-002687f61a894d1c9af65f6106be5285
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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