4-Hydroxybenzaldehyde → 4-(2-Benzyloxycarbonyl-2-methylpropoxy)benzaldehyde

HRID 2223598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223598
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.O[CH2:11][C:12]([CH3:24])([CH3:23])[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH2:16]([O:15][C:13]([C:12]([CH3:24])([CH3:23])[CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18922595Benzyl 3-hydroxy-2,2-dimethylpropanoate

Produkt 1

HCID 230778534-(2-Benzyloxycarbonyl-2-methylpropoxy)benzaldehydeAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxybenzaldehyde (2.7 g), benzyl hydroxypivalate (4.7 g) and triphenylphosphine (6.4 g) in tetrahydrofuran (22 mL) was added diethyl azodicarboxylate (40% toluene solution, 11 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-4/1) to give the title compound (0.97 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-4/1)

Quellen und Nachweise

ORD-Eintrag
ord-32f8af0f1b644c139b252f45eb078273
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375087B2

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