3-Ethylphenol → 4-Ethyl-2-hydroxybenzaldehyde

HRID 2387021

반응식

HRID 2387021 반응식
C[O:2][CH:3](Cl)Cl.[CH2:6]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[CH3:7]>[Ti](Cl)(Cl)(Cl)Cl>[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:10]=[O:14])=[C:3]([OH:2])[CH:9]=1)[CH3:7]

참가 물질

4

반응물 2

HCID 121013-EthylphenolHCID 21004Methane, dichloromethoxy-

생성물 1

HCID 102360174-Ethyl-2-hydroxybenzaldehyde수율 65.3%

시약·촉매·용매 1

HCID 24193Titanium Tetrachloride촉매

실험 절차

Titanium(IV) chloride (100 mL, 100 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (7.47 mL, 82.5 mmol) was added to a cooled 0° C. solution of 3-ethylphenol (6.11 g, 50 mmol). The reaction mixture was stirred for 45 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a bright pink oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave 4-ethyl-2-hydroxy-benzaldehyde (4.9 g, 65%) followed by 2-ethyl-4-hydroxy-benzaldehyde (1.32 g, 18%). A: 1H NMR (400 MHz, CDCl3): δ 1.25 (t, J=7.6 Hz, 3 H), 2.67 (d, J=7.6 Hz, 2 H), 6.82 (s, 1 H), 6.85 (d, J=8.0 Hz, 1 H), 7.46 (t, J=8.0 Hz, 1 H), 9.83 (s, 1 H), 11.05 (s, 1 H). B: 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.6 Hz, 3 H), 3.03 (d, J=7.6 Hz, 2 H), 6.68 (s, 1 H), 6.78 (s, 1 H), 6.82 (d, J=8.3 Hz, 1 H), 7.77 (t, J=8.3 Hz, 1 H), 10.10 (s, 1 H).

후처리

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a bright pink oil
  6. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-521b495bb2af4e898272e25ab57e6c39
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268835B2

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