2,5-Dihydroxybenzoic acid → 8-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

HRID 424312

反応式

HRID 424312 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21].C(#N)C>O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21])=[O:5]

参加物

5

反応物 3

HCID 34692,5-Dihydroxybenzoic acidHCID 6342AcetonitrileHCID 590050482-Furylmethyl 8-bromooctanoate

生成物 1

HCID 590050178-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2,5-dihydroxybenzoic acid (4.8 g), 1,8-diazobicyclo[5.5.0]undec-7-ene (4.7 g), 2-furylmethyl 8-bromooctanoate (7.8 g) and acetonitrile (150 ml) was heated, under reflux for 18 h. The cooled reaction mixture was added to water (500 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuum. The residue (8.4 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (5:1) as eluent, to give 8-(2-furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate as colourless oil.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customThe residue (8.4 g) was purified by column flash chromatography on silica gel

出典と根拠

ORDレコード
ord-a0d12cd9d8634c1b8714299d4f590676
出典データセット
uspto-grants-2012_01
特許番号
US08105662B2

関連ノート

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