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Hydrochloric Acid → Acetic acid, 6,7-dichloro-2-ethyl-2-methyl-1-oxo-5-indanyloxy-

HRID 2083445
Notes
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Reaction equation

HRID 2083445 reaction equation
[CH2:1]([C:3]1([CH3:16])[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[CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+].Cl>CN(C=O)C.O>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:24][C:25]([OH:27])=[O:26])=[C:7]([Cl:13])[C:6]=2[Cl:14])[CH2:11][C:3]1([CH2:1][CH3:2])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12395584HCID 12395584, compound

Product 1

HCID 41028Acetic acid, 6,7-dichloro-2-ethyl-2-methyl-1-oxo-5-indanyloxy-

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 2-ethyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (3.6 g., 0.014 mole), potassium carbonate (4.2 g.), ethyl bromoacetate (5.0 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 11/2 hours. The reaction mixture is poured into dilute aqueous hydrochloric acid, extracted with ether, washed with water and dried over magnesium sulfate. The ether is evaporated at reduced pressure affording the crude product which melts at 168° C. after recrystallization from nitromethane.

Workup

  1. temperatureheated on a steam bath for 11/2 hours
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ether is evaporated at reduced pressure

Sources & evidence

ORD record
ord-79f6ea3fd92b4ea7a009ec246be372fc
Source dataset
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04085219

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes