Sodium Hydroxide → 2-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acid

HRID 612566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612566
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:14])([CH3:13])[C:8]([O:10]CC)=[O:9])=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:14])([CH3:13])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21184093Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

Produkt 1

HCID 33670892-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The crude ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate was saponified by treating with 100 mL of ethanol and 100 mL of 4.0 M NaOH solution. The suspension was stirred for 3 hours, after which a clear solution formed The solution was concentrated, diluted with 150 mL of H2O, washed with 2×50 mL of ether, and acidified to pH 1 with 10% HCl solution. The aqueous phase was extracted with 3×100 mL portions of ether and the combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated leaving 18.3 g (72% yield) of racemic 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionic acid as a white solid after was recrystallization from CHCl3 and hexanes.

Aufarbeitung

  1. customafter which a clear solution formed The solution
  2. concentrationwas concentrated
  3. additiondiluted with 150 mL of H2O
  4. washwashed with 2×50 mL of ether
  5. extractionThe aqueous phase was extracted with 3×100 mL portions of ether
  6. washthe combined ether extracts were washed with 50 mL of H2O, 50 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7cecc0c8f52b4ea4ab75af19c4f49bce
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005000

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