Sodium Hydroxide → 7-[5-(2-n-Propyl-3-hydroxy-4-ethylphenoxy)pentoxy]-8-n-propylchroman-2-carboxylic acid

HRID 1285250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285250
[C:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:34][CH2:35][CH3:36])[C:9]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([OH:30])[C:23]=3[CH2:31][CH2:32][CH3:33])=[CH:10][CH:11]=2)[O:6]1)([O:3]C)=[O:2].[OH-].[Na+]>CO.O>[CH2:31]([C:23]1[C:24]([OH:30])=[C:25]([CH2:28][CH3:29])[CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:9]1[C:8]([CH2:34][CH2:35][CH3:36])=[C:7]2[C:12]([CH2:13][CH2:14][CH:5]([C:1]([OH:3])=[O:2])[O:6]2)=[CH:11][CH:10]=1)[CH2:32][CH3:33]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 202504642-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-ethylphenoxy)pentoxy]-8-n-propylchroman

Produkt 1

HCID 135378727-[5-(2-n-Propyl-3-hydroxy-4-ethylphenoxy)pentoxy]-8-n-propylchroman-2-carboxylic acidAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

1.26 g (2.5 mmole) of the methyl ester from Example 8 was dissolved in 25 ml of methanol in a single neck 100 ml round bottom flask. Next a solution of 202 mg (5 mmole) of sodium hydroxide in 10 ml water was added. The resulting mixture was stirred with the aid of a magnetic stirring bar for 2 hours at room temperature. The methanol was removed by rotary evaporation and the residue was acidified with dilute hydrochloric acid to pH 2. The acidified solution was extracted three times with 30 ml portions of ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered and the ethyl acetate removed by rotoevaporation to furnish 1.16 g (95%) of the title compound, mp 101°-102°. Calc: C, 71.87; H, 8.32; Found: C, 71.71; H, 8.31.

Aufarbeitung

  1. customThe methanol was removed by rotary evaporation
  2. extractionThe acidified solution was extracted three times with 30 ml portions of ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe ethyl acetate removed by rotoevaporation

Quellen und Nachweise

ORD-Eintrag
ord-9ffe7bd5761b4aaaaf9eed699554de84
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04565882

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