Hydrochloric Acid → HCID 21481314, compound

HRID 1659174Notes

Reaction equation

HRID 1659174 reaction equation
[CH3:1][C:2]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8]C)=[O:7].[CH2:15]([CH:17]([C:21](Cl)=[O:22])[C:18](Cl)=[O:19])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH-].[K+]>C(Cl)Cl.CO>[O:19]=[C:18]1[C:11]2[C:12](=[C:13]([CH3:14])[C:2]([CH3:1])=[C:3]([O:4][CH2:5][C:6]([OH:8])=[O:7])[CH:10]=2)[C:21](=[O:22])[CH:17]1[CH2:15][CH3:16]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 109209242-Ethylpropanedioyl dichlorideHCID 13381508Methyl (2,3-dimethylphenoxy)acetate

Product 1

HCID 21481314HCID 21481314, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl (2,3-dimethylphenoxy)acetate (3.0 g., 0.0155 mole) and 2-ethylmalonyl chloride (2.7 g., 0.016 mole) in methylene chloride (200 ml.) is cooled to 0°C. then treated with aluminum chloride (6.6 g., 0.05 mole) in several portions during a 15 minute period. The reaction is stirred for 2 hours at 0°C., 18 hours at 25°C. then at reflux for 6 hours, cooled and poured into cold 1 N-hydrochloric acid (500 ml.), the organic layer is washed with water, saturated aqueous sodium chloride, dried over magnesium sulfate, then the solvent evaporated at reduced pressure. The crude methyl ester is hydrolyzed by treatment with potassium hydroxide (0.34 g., 0.005 mole) and methanol (20 ml.) at reflux for 1/2 hour, cooled and acidified with aqueous hydrochloric acid affording (1,3-dioxo-2-ethyl-4,5-dimethyl-6-indanyloxy)acetic acid which melts at 187°-193°C. after recrystallization from acid-water.

Workup

  1. temperatureat reflux for 6 hours
  2. temperaturecooled
  3. washthe organic layer is washed with water, saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated at reduced pressure
  6. temperatureat reflux for 1/2 hour
  7. temperaturecooled

Sources & evidence

ORD record
ord-44734214379c4c369165321957fc05af
Source dataset
uspto-grants-1976_06
Patent number
US03966966

Reaction notes

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