Hydrochloric Acid → (3-Methoxy-1,2-phenylene)dimethanol

HRID 1766907노트

반응식

HRID 1766907 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][O:6][C:7]2=[O:12].[BH4-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:7][OH:12])[C:4]=1[CH2:5][OH:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONE

생성물 1

HCID 14892485(3-Methoxy-1,2-phenylene)dimethanol수율 78%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a solution of 4-methoxy-1-(3H)-isobenzofuranone (described in J. Org. Chem., 52, 129 (1987); 1.64 g, 10.0 mmol) in tetrahydrofuran (30 ml) was added lithium borohydride (652.2 mg, 30 mmol) with stirring at 0° C., and the mixture was heated under reflux for 2.5 hours with stirring. After cooling the mixture to room temperature, a 2N aqueous solution of hydrochloric acid (20 ml) was added thereto. The product was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride. The filtrate was concentrated under reduced pressure to give a solid residue. The residue was subjected to chromatography on a silica gel (30 g) column (eluent; ethyl acetate:hexane=2:1˜4:1) to afford the title compound (1.31 g, 78% yield) as a colorless solid (mp. 95° C.).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. stirringwith stirring
  4. temperatureAfter cooling the mixture to room temperature
  5. extractionThe product was extracted with ethyl acetate
  6. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a solid residue

출처 및 근거

ORD 기록
ord-00a765a01b1a4cf9a5afacf95d3269b9
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230023B2

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