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

HRID 1015456

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-0b120b38b3e34726a7fba2593289fbf9
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985353B2

Linked notes

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