Hydrochloric Acid → 1-(4-Benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid

HRID 2102991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102991
C([O:3][C:4]([C:6]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([CH3:25])[C:12]=2[CH3:26])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>CO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[C:12]([CH3:26])[C:13]=1[CH3:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 690566291-(4-Benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 690566881-(4-Benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the ester prepared as above (0.78 g) in MeOH (20 mL), was added NaOH solution (10% wt, 3 mL) and water (2 mL). After stirring the solution at 50° C. for 4 h it was poured into water, and diluted HCl solution was added to adjust pH to 3. The mixture was partitioned between EtOAc and water, and the organic layer was washed with water, dried over MgSO4 and evaporated. The residue was purified by silica gel column eluting with 40% EtOAc in hexane to give 0.6 g of 1-(4-benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid as a pale solid.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was partitioned between EtOAc and water
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by silica gel column
  7. washeluting with 40% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-be34c227fc104e628df7abee84d83988
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

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