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

HRID 1766914노트

반응식

HRID 1766914 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2.[BH4-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:7][OH:8])[C:10]=1[CH2:9][OH:11]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6387577-methyl-2-benzofuran-1(3H)-oneHCID 4148881Lithium borohydride

생성물 1

HCID 22155097(3-Methyl-1,2-phenylene)dimethanol수율 19%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

A solution of the 7-methyl-1(3H)-isobenzofuranone obtained above in tetrahydrofuran (80 ml) was cooled to 0° C., and lithium borohydride (1.90 g, 87.2 mmol) was added thereto. The mixture was stirred at 60° C. for 2 hours, then cooled to 0° C., and a 2N aqueous solution of hydrochloric acid (50 ml) was added dropwise. The product was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (75 g) column (eluent; ethyl acetate:hexane=2:1˜1:0) to afford the title compound (4.17 g, 19% total yield from methyl 2,6-dimethylbenzoate) as an oil.

후처리

  1. temperaturecooled to 0° C.
  2. extractionThe product was extracted with ethyl acetate
  3. customthe solvent was evaporated under reduced pressure
  4. customto give an oily residue

출처 및 근거

ORD 기록
ord-27b1a56507854675bcbefc3e56b414a1
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230023B2

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