2-Ethyl-5-methylphenol → 5-Ethyl-4-hydroxy-2-methyl-benzaldehyde

HRID 858856

反応式

HRID 858856 の反応式
[CH3:1][O:2]C(Cl)Cl.[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[OH:15])[CH3:7]>[Ti](Cl)(Cl)(Cl)Cl>[CH2:6]([C:8]1[C:9]([OH:15])=[CH:10][C:11]([CH3:14])=[C:12]([CH:13]=1)[CH:1]=[O:2])[CH3:7]

参加物

4

反応物 2

HCID 155232-Ethyl-5-methylphenolHCID 21004Methane, dichloromethoxy-

生成物 1

HCID 587624205-Ethyl-4-hydroxy-2-methyl-benzaldehyde収率 50%

試薬・触媒・溶媒 1

HCID 24193Titanium Tetrachloride触媒

実験手順

Titanium(IV) chloride (11 mL, 11 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (1.04 g, 9.1 mmol) was added to a cooled 0° C. solution of 2-ethyl-5-methyl-phenol (0.75 g, 5.5 mmol) The reaction mixture was stirred for 30 mins and then warmed up to rt and stirred for another 30 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a purple oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as an oil (0.45 g, 50%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3 H), 2.60 (s, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 5.37 (s, 1 H), 6.62 (s, 1 H), 7.62 (s, 1 H), 10.11 (s, 1 H).

後処理

  1. stirringstirred for another 30 mins
  2. additionThe mixture was poured into ice
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with satd NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a purple oil
  7. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-6f200c5e6a834706a8edd9a9a298e498
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

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