Formaldehyde → Isochromane

HRID 432939

반응식

HRID 432939 반응식
[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

참가 물질

5

반응물 2

HCID 712FormaldehydeHCID 60542-Phenylethanol

생성물 1

HCID 96266Isochromane수율 40.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea6d30e65e78480b9795e5e78a3f3f98
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664380B1

연결된 노트

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