Ethyl bromoacetate → (1-Oxo-2,2-diethyl-6,7-dichloro-5-indanyloxy)acetic Acid

HRID 1287435Notes

Reaction equation

HRID 1287435 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([Cl:14])[C:7]([Cl:13])=[C:8]([OH:12])[CH:9]=2)[C:4]1=[O:15])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+]>CN(C=O)C.O>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:25][C:26]([OH:28])=[O:27])=[C:7]([Cl:13])[C:6]=2[Cl:14])[CH2:11][C:3]1([CH2:1][CH3:2])[CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 203584452,2-Diethyl-5-hydroxy-6,7-dichloro-1-indanone

Product 1

HCID 20358467(1-Oxo-2,2-diethyl-6,7-dichloro-5-indanyloxy)acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 2,2-diethyl-5-hydroxy-6,7-dichloro-1-indanone (3.6 g., 0.013 mole), potassium carbonate (4.2 g.) and ethyl bromoacetate (5 g.) in DMF (40 ml.) is warmed in an inert atmosphere at 55° C. for one hour, then treated with water (40 ml.) and 10N sodium hydroxide (6 ml.) and heated on a steam bath for 1.5 hours. The reaction mixture is poured into ice water (200 ml.), acidified, then extracted with ether, washed with water and dried over magnesium sulfate. Following evaporation of the ether the residue is crystallized from butyl chloride affording 1.3 g. of (1-oxo-2,2-diethyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 111° C.

Workup

  1. temperatureheated on a steam bath for 1.5 hours
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporation of the ether the residue
  6. customis crystallized from butyl chloride affording 1.3 g

Sources & evidence

ORD record
ord-744ac0bd786b4073bc102fdf09b8143a
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

Loading…