Hydrochloric Acid → HCID 86736981, Verbindung

HRID 894974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894974
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[O:14]1[C@H:16]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15]1.Cl>CO>[CH2:19]([O:18][CH2:17][C@H:16]([OH:14])[CH2:15][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 146296(+)-Benzyl glycidyl etherHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 5360545Sodium

Produkt 1

HCID 86736981HCID 86736981, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

Sodium (2.3 g; 0.1 mol) was dissolved in 500 ml anhydrous MeOH and to this was added a solution of 194.3 g (1.17 mol) 4-hydroxyphenylacetic acid, methyl ester in 250 ml MeOH followed by a solution of 167.3 g. (1.018 mol) (S)-1,2-epoxy-3-benzyloxypropane in 250 ml MeOH. The solution was stirred under reflux for 12 hours. The cooled solution was treated with 8.3 ml (0.1 mol) of concentrated HCl and the methanol was removed in vacuo. The crude product was dissolved in benzene and washed with 2×200 ml portions of cold 1 N NaOH solution and with H2O (1×300 ml). The aqueous layers were backwashed with benzene (2×500 ml). The combined organic layers were dried (Na2SO4) and evaporated in vacuo to give crude (S)-4-(3-benzyloxy-2-hydroxypropoxy)phenyl acetic acid, methyl ester.

Aufarbeitung

  1. temperatureunder reflux for 12 hours
  2. customthe methanol was removed in vacuo
  3. dissolutionThe crude product was dissolved in benzene
  4. washwashed with 2×200 ml portions of cold 1 N NaOH solution and with H2O (1×300 ml)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c004d78864c42a68af8a46ccfb50e91
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04285873

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