Ethyl bromoacetate → HCID 21483911, compound

HRID 1415205Notes

Reaction equation

HRID 1415205 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:13])[C:11]=1[Cl:12])[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25]CC)=[O:24].[OH-].[K+]>CN(C=O)C.CO.O>[O:14]=[C:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH2:22][C:23]([OH:25])=[O:24])=[C:11]([Cl:12])[C:10]=2[Cl:13])[CH2:5][CH2:6][CH2:7]1

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 21483904HCID 21483904, compound

Product 1

HCID 21483911HCID 21483911, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 6-hydroxy-7,8-dichloro-1-tetralone (1 g., 0.0044 mole), potassium carbonate (10.69 g., 0.005 mole) and ethyl bromoacetate (0.84 g., 0.005 mole) in DMF (20 ml.) is heated at 60° C. for 11/2 hours. A solution of potassium hydroxide (0.45 g., 0.008 mole) in methanol (40 ml.) is added, the mixture is refluxed for one-half hour and then poured into water (ca. 500 ml.). Upon acidification a white powder separates. It is collected, washed with water, dried and crystallized from ethanol to obtain (1-oxo-7,8-dichloro-1,2,3,4-tetrahydro-6-naphthyloxy)-acetic acid (1.1 g.), melting point 250°-252° C.

Workup

  1. temperaturethe mixture is refluxed for one-half hour
  2. customIt is collected
  3. washwashed with water
  4. customdried
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-7cea7f0ce4db4a13ad73d324d66064bf
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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