3-Hydroxybenzaldehyde → 3-Tert-butoxybenzaldehyde

HRID 990550노트

반응식

HRID 990550 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 157122243-Tert-butoxybenzaldehyde수율 32%

시약·촉매·용매 4

HCID 6344Dichloromethane용매2회HCID 8058Hexane용매HCID 8078Cyclohexane용매HCID 8857Ethyl Acetate용매

실험 절차

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 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3c51b92ef3e54b4e9122d4a5fcbf60e1
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458852B1

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