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

HRID 1766914ノート

反応式

HRID 1766914 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

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

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.

後処理

  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

出典と根拠

ORDレコード
ord-27b1a56507854675bcbefc3e56b414a1
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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