3-Hydroxybenzaldehyde → 3-Tert-butoxybenzaldehyde

HRID 990443

Reaktionsgleichung

Reaktionsgleichung von HRID 990443
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10](OC(=N)C(Cl)(Cl)Cl)([CH3:13])([CH3:12])[CH3:11].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C1CCCCC1.CCCCCC.C(OCC)(=O)C>[C:10]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])([CH3:12])[CH3:11]

Komponenten

9

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Produkt 1

HCID 157122243-Tert-butoxybenzaldehydeAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8078CyclohexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

EX-654A) 3-Hydroxybenzaldehyde (4.08 g, 33.4 mmol) was slurried in 50 mL of anhydrous CH2Cl2 and added to t-butyl-2,2,2-trichloroacetimidate (25.0 g, 114 mmol) in 200 mL of anhydrous cyclohexane with an additional 50 mL of CH2Cl2 used in transfer. The mixture was stirred under nitrogen until uniform, then boron trifluoride diethyl etherate (0.50 mL, 4 mmol) was added via syringe and stirring was continued for 1 h. Powdered sodium bicarbonate (50 g, 0.6 mmol) was added, and the solution was filtered through a silica gel plug, washing the plug with hexane. The solvent was evaporated to give crude product 3.54 g (59%) as an amber oil (85% pure by GC analysis). Chromatography on silica gel eluting with 0-10% ethyl acetate in hexane gave 1.88 g (32%) of pure 3-t-butoxybenzaldehyde product as a colorless oil. 1H NMR (C6D6) δ9.59 (s, 1H), 7.44 (br s, 1H), 7.20 (d t, 1H), 6.92 (m, 2H), 1.07 (s, 9H).

Aufarbeitung

  1. stirringstirring
  2. filtrationthe solution was filtered through a silica gel plug
  3. washwashing the plug with hexane
  4. customThe solvent was evaporated
  5. customto give crude product 3.54 g (59%) as an amber oil (85% pure by GC analysis)

Quellen und Nachweise

ORD-Eintrag
ord-44f52485bf874692b811ec8717f154ad
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458803B1

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