Water → 3,3',4,4'-Tetra(hydroxymethyl)-1,1'-biphenyl

HRID 1015456

反応式

HRID 1015456 の反応式
[CH:1]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]3[C:13]([O:15][C:16](=O)[C:9]=3[CH:8]=2)=[O:14])=[CH:5][C:4]2[C:18]([O:20][C:21](=O)[C:3]=2[CH:2]=1)=[O:19].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[OH:15][CH2:16][C:9]1[CH:8]=[C:7]([C:6]2[CH:1]=[CH:2][C:3]([CH2:21][OH:20])=[C:4]([CH2:18][OH:19])[CH:5]=2)[CH:12]=[CH:11][C:10]=1[CH2:13][OH:14]

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 754945,5'-Bi-2-benzofuran-1,1',3,3'-tetroneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 597794533,3',4,4'-Tetra(hydroxymethyl)-1,1'-biphenyl収率 55.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
100 °C

実験手順

To a solution of 3,3′,4,4′-biphenyltetracarboxylic dianhydride (6.0 g, 20.4 mmol, 1.0 molar equivalent) in THF (600 mL) heated to 100° C. is added carefully a solution of LiAlH4 (1M in tetrahydrofuran) (81 mL, 81.6 mmol, 2.0 molar equivalents). The reaction mixture is stirred overnight at 100° C. To this resulting solution cooled at 0° C. is added a 2M sodium hydroxide solution (50 mL) followed by cold water (25 mL) and THF (50 mL). The reaction mixture is then filtered and concentrated under vacuum. The crude product is then washed with THF (20 mL), water (10 mL) and dried over vacuum to give a white powder (3.1 g, 55%). If necessary, the compound can be further purified by recrystallisation in water to give the expected compound as a white powder (3.3 g, 79%). 1H NMR (300.13 MHz, DMSO) δ (ppm) 4.57 (d, J=4.5 Hz, 4H) 4.61 (d, J=4.5 Hz, 4H) 5.09 (t, J=5.2 Hz, 2H) 5.15 (t, J=5.2 Hz, 2H) 7.46 (d, J=8.1 Hz, 2H) 7.52 (dd, J1=8.1, J2=1.8 Hz, 2H) 7.70 (d, J=1.8 Hz, 2H).

後処理

  1. temperatureTo this resulting solution cooled at 0° C.
  2. filtrationThe reaction mixture is then filtered
  3. concentrationconcentrated under vacuum
  4. washThe crude product is then washed with THF (20 mL), water (10 mL)
  5. customdried over vacuum

出典と根拠

ORDレコード
ord-0b120b38b3e34726a7fba2593289fbf9
出典データセット
uspto-grants-2011_07
特許番号
US07985353B2

関連ノート

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