4,6,4',6'-Tetramethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester → (6'-Hydroxymethyl-4,6,2',4'-tetramethoxy-biphenyl-2-yl)-methanol

HRID 72002Notes

Reaction equation

HRID 72002 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:15]2[C:16]([C:25](OC)=[O:26])=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=2[O:21][CH3:22])=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][C:5]1[C:6]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=2[CH2:25][OH:26])=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

4

Reactant 2

HCID 120747334,6,4',6'-Tetramethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 10958571(6'-Hydroxymethyl-4,6,2',4'-tetramethoxy-biphenyl-2-yl)-methanolYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,6,4′,6′-tetramethoxy-biphenyl-2,2′-dicarboxylic acid dimethyl ester (2.5 g) was dissolved in THF (96 mL), and 1M LiAlH4 in THF (9.6 mL) was added. After stirring at room temperature for overnight, the mixture was quenched with water and 2N HCl (24 mL) was added. The mixture was evaporated under vacuum and partitioned with DCM (300 mL) and water (200 mL). The organic layer was dried over Na2SO4 and crystallized with DCM to provide (6′-hydroxymethyl-4,6,2′,4′-tetramethoxy-biphenyl-2-yl)-methanol (1.7 g, 77%) as a pale blue white triclinic crystals.

Workup

  1. customthe mixture was quenched with water and 2N HCl (24 mL)
  2. additionwas added
  3. customThe mixture was evaporated under vacuum
  4. custompartitioned with DCM (300 mL) and water (200 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customcrystallized with DCM

Sources & evidence

ORD record
ord-671868e92f1e47e1adae32150c829d3d
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

Loading…