Hydrochloric Acid → HCID 13300595, compound

HRID 1903207Notes

Reaction equation

HRID 1903207 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:17]=[CH:16][C:9]2[CH2:10][CH:11]([C:13]([OH:15])=[O:14])[O:12][C:8]=2[C:7]=1[Cl:18].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].Cl>>[Cl:5][C:6]1[C:17]([C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=2)=[CH:16][C:9]2[CH2:10][CH:11]([C:13]([OH:15])=[O:14])[O:12][C:8]=2[C:7]=1[Cl:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 98160656,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic Acid

Product 1

HCID 13300595HCID 13300595, compound

Conditions

Temperature
90 °C

Procedure

Anhydrous aluminum chloride (5.97 g., 0.0448 mole) was added in small portions to a stirred mixture of 2.6 g. (0.0112 mole) of 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid and 6.24 g. (0.0336 mole) of 4-nitrobenzoyl chloride. The mixture was heated at 90° C. for 4 hours and then poured into 170 ml. of ice water and 10 ml. of concentrated hydrochloric acid. The product was extracted into ethyl acetate (200 ml.), washed with water, and then extracted with 5% aqueous sodium bicarbonate (100 ml.) from which the sodium salt of the product precipitated. The sodium salt of the product was filtered and transferred to a separatory funnel with 2 N hydrochloric acid (70 ml.) and ethyl acetate (150 ml.) and shaken until the solid dissolved. The ethyl acetate solution was washed with water, dried over sodium sulfate and evaporated in vacuo. The product was recrystallized from acetic acid; m.p. 243°-245°.

Workup

  1. additionpoured into 170 ml
  2. extractionThe product was extracted into ethyl acetate (200 ml.)
  3. washwashed with water
  4. extractionextracted with 5% aqueous sodium bicarbonate (100 ml.) from which the sodium salt of the product
  5. customprecipitated
  6. filtrationThe sodium salt of the product was filtered
  7. customtransferred to a separatory funnel with 2 N hydrochloric acid (70 ml.) and ethyl acetate (150 ml.)
  8. dissolutiondissolved
  9. washThe ethyl acetate solution was washed with water
  10. dry with materialdried over sodium sulfate
  11. customevaporated in vacuo
  12. customThe product was recrystallized from acetic acid

Sources & evidence

ORD record
ord-32c93b55aded4a14be9fc3827a4d377c
Source dataset
uspto-grants-1984_03
Patent number
US04435422

Reaction notes

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