Water → (1-Benzylcyclohex-2-en-1-yl)acetic acid

HRID 1292752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292752
[O-]Cl=O.[Na+].[OH2:5].[CH2:6]([C:13]1([CH2:19][CH:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CS(C)=O.CCOCC>[CH2:6]([C:13]1([CH2:19][C:20]([OH:5])=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 22243087(1-Benzylcyclohex-2-en-1-yl)acetaldehydeHCID 23668197Sodium Chlorite

Produkt 1

HCID 22243083(1-Benzylcyclohex-2-en-1-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of NaH2PO4 (55.3 g), NaClO2 (36.3 g), DMSO (200 mL) and water (375 mL) was added a solution of 3-benzyl-3-formylmethylcyclohexene (57 g) in DMSO (150 mL) during a 3 hour period. After addition, the mixture was stirred overnight and diluted with ether (200 mL). This was extracted with saturated NaHCO3 (3×100 mL). The combined aqueous layer was cooled to 0° C. and acidified to PH=1 with conc. HCl. This was extracted with CH2Cl2 (3×300 mL). The combined organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as thick oil (50 g). MS (MH+=231).

Aufarbeitung

  1. additionAfter addition
  2. extractionThis was extracted with saturated NaHCO3 (3×100 mL)
  3. extractionThis was extracted with CH2Cl2 (3×300 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c7d9da485ff04c5f8e6912c91821b891
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238687B2

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