Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate → HCID 59509487、化合物

HRID 2407473ノート

反応式

HRID 2407473 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][C:13]([CH3:15])=[CH2:14])[CH:6]=1)[CH3:2]>C(O)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][C:13]([CH3:15])([CH3:14])[CH2:12][C:7]=2[CH:6]=1)=[O:16])[CH3:2]

参加物

3

反応物 1

HCID 18705333Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

生成物 1

HCID 59509487HCID 59509487、化合物

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
110 °C

実験手順

A mixture of formic acid (12 mL) and 4-hydroxy-3-(2-methylprop-2-enyl)benzoic acid ethyl ester (4.8 g, 0.022 mol) is heated at 110° C. for 15 minutes. The reaction mixture is cooled to room temperature and formic acid is removed under reduced pressure. Demineralized water is added to the residue and the aqueous layer is extracted with dichloromethane (3×15 mL). Combined organic layers are washed with demineralized water (1×15 mL) followed by brine (1×15 mL) and dried over sodium sulphate. Removal of solvent gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 90:10) to give 2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carboxylic acid ethyl ester.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customformic acid is removed under reduced pressure
  3. additionDemineralized water is added to the residue
  4. extractionthe aqueous layer is extracted with dichloromethane (3×15 mL)
  5. washCombined organic layers are washed with demineralized water (1×15 mL)
  6. dry with materialdried over sodium sulphate
  7. customRemoval of solvent
  8. customgives a viscous liquid which
  9. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 90:10)

出典と根拠

ORDレコード
ord-d44d9b3fb5a6405b95a1653d12cc8f13
出典データセット
uspto-grants-2014_08
特許番号
US08809539B2

反応ノート

読み込み中…