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

HRID 1766907ノート

反応式

HRID 1766907 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-00a765a01b1a4cf9a5afacf95d3269b9
出典データセット
uspto-grants-2007_06
特許番号
US07230023B2

反応ノート

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