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

HRID 1015456

반응식

HRID 1015456 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0b120b38b3e34726a7fba2593289fbf9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985353B2

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