Hydrochloric Acid → 3-(p-Cyclohexyloxybenzoyl)propionic acid

HRID 371997

Reaktionsgleichung

Reaktionsgleichung von HRID 371997
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[O:8]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[CH:15]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:4]([CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[O:5])=[CH:11][CH:10]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 137492Benzene, (cyclohexyloxy)-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 203526303-(p-Cyclohexyloxybenzoyl)propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of succinic anhydride (20 g.) and phenoxycyclohexane (35.1 g.) in 1,2-dichloroethane (250 ml.) was stirred at 0° C and treated with powdered anhydrous aluminium chloride (58.2 g.) and stirring was continued for 5 hours at 0°-5° C. It was then poured carefully with stirring into ice-water (1 liter) containing concentrated hydrochloric acid (100 ml.). The organic layer was separated, washed with water and extracted with a solution of sodium hydroxide (8 g.) in water (250 ml.). The alkaline extract was adjusted to pH 4-6 by the addition of dilute hydrochloric acid to yield the product (6.8 g.), m.p. 190°-192° C after crystallisation from aqueous methanol.

Aufarbeitung

  1. additionIt was then poured carefully
  2. customThe organic layer was separated
  3. washwashed with water
  4. extractionextracted with a solution of sodium hydroxide (8 g.) in water (250 ml.)
  5. extractionThe alkaline extract
  6. additionwas adjusted to pH 4-6 by the addition of dilute hydrochloric acid
  7. customto yield the product (6.8 g.), m.p. 190°-192° C
  8. customafter crystallisation from aqueous methanol

Quellen und Nachweise

ORD-Eintrag
ord-3de6d33631a9455b9b4da2f7548e7a61
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088762

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