Hydrochloric Acid → 4-Heptyloxy-2-chlorobenzoic acid

HRID 437011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437011
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].Cl>O.C(O)C>[CH2:13]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Cl:1])[CH:10]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 123691-BromoheptaneHCID 14797Potassium Hydroxide2×HCID 918212-Chloro-4-hydroxybenzoic acid

Produkt 1

HCID 40208144-Heptyloxy-2-chlorobenzoic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

A mixture of 4.0 parts of 2-chloro-4-hydroxybenzoic acid, 8.3 parts of 1-bromoheptane, 2.6 parts of potassium hydroxide, 10 parts of water and 90 parts by volume of ethanol was refluxed for 20 hours. A solution of 2.5 parts of potassium hydroxide in 50 parts of water was then added and refluxing continued for an additional 1.5 hours. The reaction mixture was diluted with 100 parts of water, acidified with concentrated hydrochloric acid and extracted with methylene chloride. The combined extracts were dried over sodium sulfate, the solvent evaporated and the resultant residue recrystallized from hexane. 4.5 Parts of 4-heptyloxy-2-chlorobenzoic acid (75% yield) was obtained having a melting point of 76°-78° C.

Aufarbeitung

  1. temperaturewas refluxed for 20 hours
  2. temperaturerefluxing
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customthe solvent evaporated
  6. customthe resultant residue recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-2b5adc3c19c446858a5a7140b6c612b4
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029594

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