Methanol → [3-(hydroxymethyl)-2-nitrophenyl]methanol

HRID 1380650ノート

反応式

HRID 1380650 の反応式
[N+:1]([C:4]1[C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](O)=[O:14])([O-:3])=[O:2].B.CO>O1CCCC1>[N+:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][OH:14])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 887MethanolHCID 6331BoraneHCID 888062-Nitroisophthalic acid

生成物 1

HCID 13519807[3-(hydroxymethyl)-2-nitrophenyl]methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of 2-nitro-1,3-benzenedicarboxylic acid (12.7 g, 0.06 mole) in tetrahydrofuran (60 ml) is cooled to 0° C. and 1N borane:tetrahydrofuran (300 ml, 0.3 mole) is added dropwise over one hour. The mixture is allowed to warm slowly to 25° C. and is stirred for 36 hours. Methanol (50 ml) is added slowly, the mixture is filtered and evaporated. The residue is dissolved in ethyl acetate (100 ml) and washed with water (25 ml), dried (MgSO4), filtered, and evaporated to yield a yellow solid. This is further purified by flash chromatography over silica (elution with 1:1 hexane:ethyl acetate) to afford after concentration pure 2-nitro-1,3-benzenedimethanol, mp 100°-101° C.

後処理

  1. filtrationthe mixture is filtered
  2. customevaporated
  3. dissolutionThe residue is dissolved in ethyl acetate (100 ml)
  4. washwashed with water (25 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a yellow solid
  9. customThis is further purified by flash chromatography over silica (elution with 1:1 hexane:ethyl acetate)
  10. customto afford
  11. concentrationafter concentration pure 2-nitro-1,3-benzenedimethanol, mp 100°-101° C.

出典と根拠

ORDレコード
ord-2bae8f2064e54d869fe74c0472a1f733
出典データセット
uspto-grants-1986_04
特許番号
US04582909

反応ノート

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