Ethyl bromoacetate → HCID 21483949, compound

HRID 1415201Notes

Reaction equation

HRID 1415201 reaction equation
[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([Cl:18])[C:10]([Cl:17])=[C:11]([OH:16])[CH:12]=3)[C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:21][C:22]([O:24]CC)=[O:23].[OH-].[K+]>C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>[O:19]=[C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:16][CH2:21][C:22]([OH:24])=[O:23])=[C:10]([Cl:17])[C:9]=2[Cl:18])[CH2:14][CH2:15][CH:6]1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 21483899HCID 21483899, compound

Product 1

HCID 21483949HCID 21483949, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Procedure

2-Cyclopentyl-6-hydroxy-7,8-dichloro-1-tetralone (9.45 g., 0.03 mole) is heated in a mixture of potassium carbonate (5.52 g.) and ethyl bromoacetate (6.68 g., 0.04 mole) in DMF 70 ml.) at 55°-60° C. for three hours. Potassium hydroxide (2.24 g., 0.04 mole) is added. This solution is added to the reaction mixture and the whole is refluxed for 1 hour. Most of the methanol is evaporated and the residue is added to water (ca. 200 ml.). The solid that separates upon acidification is collected, washed with water and crystallized from ethanol to obtain (1-oxo-2-cyclopentyl-7,8-dichloro-1,2,3,4-tetrahydro-6-naphthyloxy)acetic acid.

Workup

  1. additionThis solution is added to the reaction mixture
  2. temperaturethe whole is refluxed for 1 hour
  3. customMost of the methanol is evaporated
  4. additionthe residue is added to water (ca. 200 ml.)
  5. customThe solid that separates upon acidification is collected
  6. washwashed with water
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-bd205683790a4730938c28542b345c06
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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