반응 #76349

반응 방정식

sodium bicarbonate

3-Hydroxybenzaldehyde

t-butyl-2,2,2-trichloroacetimidate

boron trifluoride diethyl etherate

→

3-t-butoxybenzaldehyde

수율 32.0%

용매

hexane

ethyl acetate

cyclohexane

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   여과the solution was filtered through a silica gel plug
3. 3
   세척washing the plug with hexane
4. 4
   기타The solvent was evaporated
5. 5
   기타to give crude product 3.54 g (59%) as an amber oil (85% pure by GC analysis)

실험 절차

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 μL, 4 mmol) was added via syringe and stirring was continued for 1 h. Powdered sodium bicarbonate (50 g, 0.6 mol) 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).

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