Formaldehyde → Isochromane

HRID 432939

反応式

HRID 432939 の反応式
[CH2:1]([OH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]=O>C(O)(=O)C.C(Cl)Cl>[CH2:10]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][O:9]1

参加物

5

反応物 2

HCID 712FormaldehydeHCID 60542-Phenylethanol

生成物 1

HCID 96266Isochromane収率 40.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of phenethyl alcohol (122 mg, 1.0 mmol) in glacial acetic acid (2 mL) was added formaldehyde (40% in water, 100 μl, 1.5 mmol) and Yb(CNf3)3 (276 mg, 0.1 mmol, 10 mol %). The mixture was stirred at reflux for 18 hours. The mixture was allowed to cool, diluted with CH2Cl2, washed with water, aqueous sodium hydrogen carbonate solution, and brine, dried over MgSO4, filtered and evaporated. Chromatography (3:1 PE:Et2O) gave isochroman (54 mg, 40%) as a colourless oil: IR (thin film; NaCl plate) 2929, 2851, 1605, 1585 cm−1; δH (300 MHz, CDCl3) 7.23-7.14 (3H, m, Ar—H×3), 7.04-7.00 (1H, m, Ar—H), 4.82 (2H, s, ArCH2O), 4.04 (2H, t, J=5.7 Hz, ArCH2OCH2), 2.90 (2H, t, J=5.7 Hz, ArCH2CH2); δC (75 MHz, CDCl3) 135.0, 133.3, 129.0, 126.4, 126.0, 124.4, 68.0, 65.4, 28.4; MS 134 (M+), 104, 77, 51.

後処理

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. washwashed with water, aqueous sodium hydrogen carbonate solution, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ea6d30e65e78480b9795e5e78a3f3f98
出典データセット
uspto-grants-2003_12
特許番号
US06664380B1

関連ノート

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