Water → 4,4-Bis(Hydroxymethyl)Biphenyl

HRID 963575

Reaction equation

HRID 963575 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=O)=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10](C(OC)=O)=[CH:9][CH:8]=1.O.OS(O)(=O)=O.C1C[O:36][CH2:35]C1>>[OH:36][CH2:35][C:20]1([CH2:23][OH:25])[CH:19]=[CH:18][C:17]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:22][CH2:21]1

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 8028Tetrahydrofuran2×HCID 13099Dimethyl 4,4'-biphenyldicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 687435014,4-Bis(Hydroxymethyl)BiphenylYield 93%

Conditions

Temperature
-20 °C

Procedure

In a 1000 ml three-necked flask, fitted with an efficient condenser, a thermometer and a dropping funnel, is placed a suspension of 6,2 g (0.144 mol) LiAlH4 in 80 ml dry THF under an inert atmosphere. A solution of 30 g (0.122 mol) dimethyl 4,4'-biphenyldicarboxylate in 250 ml dry THF is added dropwise over a period of 30 minutes. The mixture is refluxed with stirring for 1 hour. The mixture is cooled to -20° C. and 80 ml of H2O is added dropwise, followed by slow addition of 80 ml of 20% H2SO4 (aq.). The THF is evaporated under reduced pressure to give a suspension of colourless product in aqueous acid. The product is filtered and washed with H2O. After recrystallisation from aceton, white crystals are obtained. Yield: 93%; melting point: 187.3° C.-188.5° C.

Workup

  1. customIn a 1000 ml three-necked flask, fitted with an efficient condenser
  2. temperatureThe mixture is refluxed
  3. customThe THF is evaporated under reduced pressure
  4. customto give
  5. additiona suspension of colourless product in aqueous acid
  6. filtrationThe product is filtered
  7. washwashed with H2O
  8. customAfter recrystallisation from aceton, white crystals
  9. customare obtained

Sources & evidence

ORD record
ord-63b2289b48a74ce58fc15c0884e38cf7
Source dataset
uspto-grants-1998_06
Patent number
US05763539

Linked notes

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