Water → (3-Methoxy-1,2-phenylene)dimethanol

HRID 505252노트

반응식

HRID 505252 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[O:9][CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(Cl)Cl>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[CH2:10][OH:12]

참가 물질

6

반응물 4

HCID 962Water2회HCID 6344DichloromethaneHCID 109865837-methoxy-3H-isobenzofuran-1-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14892485(3-Methoxy-1,2-phenylene)dimethanol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 7-methoxy-3H-isobenzofuran-1-one (16.65 g, 101.4 mmol) in anhydrous THF (200 ml) was added at room temperature under an atmosphere of argon to a freshly prepared solution of LiAlH4 (7.70 g, 202.8 mmol, 2.0 equiv) in THF (100 ml). After 30 minutes at room temperature, TLC analysis indicated complete conversion. The reaction mixture was cooled to 0° C. and water was added dropwise until gas evolution ceased. Water (500 ml) and CH2Cl2 (500 ml) was added to form a white suspension. After filtration, the filtrate was extracted with CH2Cl2 (4 liters in total). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (15.34 g, 90%) in adequate purity for direct use in the next transformation. 1H NMR (400 MHz, CDCl3): δ=7.27 (t, J=7.8 Hz, 1H), 6.96 (d, J=7.3 Hz, 1H), 6.89 (d, J=8.3 Hz, 1H), 4.83 (s, 2H); 4.72 (s, 2H), 3.85 (s, 3H), 2.8-2.6 (br s, 2H). MS (ES+): 169 (M+H)+.

후처리

  1. customto form a white suspension
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with CH2Cl2 (4 liters in total)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7a5900d4dcb64bf0b912e8bad28fb2b4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781438B2

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