Water → Methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate

HRID 1393848ノート

反応式

HRID 1393848 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22].O>CC(C)=O>[CH3:22][C:21]([CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

生成物 1

HCID 69306599Methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate収率 92.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Methyl 4-hydroxyphenylacetate (6.00 g, 36.11 mmol) was dissolved in acetone (90 ml), and then potassium carbonate (9.98 g, 72.22 mmol) and geranyl bromide(14.34 ml, 72.22 mmol) were added thereto. After being refluxed for 4 hours, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride water and saturated brine successively, and dried over MgSO4. The solvent was evaporated out and the obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane), to give methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate (10.07 g, 92%).

後処理

  1. temperatureAfter being refluxed for 4 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated ammonium chloride water and saturated brine successively
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated out
  6. customthe obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-08dd9b8c067f4662880f983f1bca2556
出典データセット
uspto-grants-2008_03
特許番号
US07348017B2

反応ノート

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