2-Methyl-2-butene → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid

HRID 1094299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094299
[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[O-:25]Cl=O.[Na+]>C(O)(C)(C)C.O.CC(OC)(C)C>[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][C:12]([C:13]([OH:25])=[O:14])=[CH:11][C:10]=1[CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 866393484-Benzyloxy-3-ethyl-5-methylbenzaldehyde

Produkt 1

HCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a mixture of 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (132 g, 0.519 mol) and 2-methyl-2-butene (364 g, 5.19 mol) in tert.-butanol (1500 mL), a solution of NaH2PO4 dihydrate (249 g, 2.08 mol) in water (1500 mL) is added. To this mixture, NaClO2 (187.8 g, 2.08 mol) is added in portions. The temperature of the reaction mixture is kept below 30° C., and evolution of gas is observed. Upon completion of the addition, the orange bi-phasic mixture is stirred well for 3 h before it is diluted with TBME (1500 mL). The org. layer is separated and washed with 20% aq. NaHS solution (1500 mL) and water (500 mL). The org. phase is then extracted three times with 0.5 N aq. NaOH (1000 mL), the aqueous phase is acidified with 25% aq. HCl (500 mL) and extracted twice with TBME (1000 mL). These org. extracts are combined and evaporated to dryness to give 4-benzyloxy-3-ethyl-5-methyl-benzoic acid; 1H NMR (D6-DMSO): δ 1.17 (t, J=7.5 Hz, 3H), 2.31 (s, 3H), 2.67 (q, J=7.5 Hz, 2H), 4.86 (s, 2H), 7.34-7.53 (m, 5H), 7.68 (s, 2H), 12.70 (s, 1H).

Aufarbeitung

  1. customis kept below 30° C.
  2. additionUpon completion of the addition
  3. customlayer is separated
  4. washwashed with 20% aq. NaHS solution (1500 mL) and water (500 mL)
  5. extractionphase is then extracted three times with 0.5 N aq. NaOH (1000 mL)
  6. extractionextracted twice with TBME (1000 mL)
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-472f8d70db5044a59c9b6baf074761df
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133910B2

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