Lithium Hydroxide → 3',4',5'-Trimethoxy-biphenyl-2-carboxylic acid

HRID 2075936Notes

Reaction equation

HRID 2075936 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-]>CO>[CH3:22][O:21][C:13]1[CH:12]=[C:11]([C:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:16]=[C:15]([O:17][CH3:18])[C:14]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 597857033',4',5'-Trimethoxy-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 597857043',4',5'-Trimethoxy-biphenyl-2-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 3′,4′,5′-Trimethoxy-biphenyl-2-carboxylic acid methyl ester (55) (626 mg, 2.08 mmol) in MeOH (14 mL) at rt and add 1M aqu LiOH (4.2 mL, 4.20 mmol). Stir reaction mixture for 8 h under reflux. Remove solvent and partition the residue between 1 M aqu. HCl and EtOAc, separate layers, extract the aqu. layer with EtOAc (3×), wash the combined organic layer with brine and dry with Na2SO4. Remove solvent and recrystallize residue from EtOAc/CyH 1+2 to obtain 3′,4′,5′-Trimethoxy-biphenyl-2-carboxylic acid (56) as a white solid (423 mg, 79%). 1H NMR (400 MHz, CD3OD: 3.84 (s, 3H); 3.89 (s, 6H); 6.68 (s, 2H); 7.42-7.49 (m, 2H); 7.57 (t, 1H, J=7.5 Hz); 7.76 (d, 1H, J=8.0 Hz).

Workup

  1. customreaction mixture for 8 h
  2. temperatureunder reflux
  3. customRemove solvent and partition the residue between 1 M aqu
  4. customHCl and EtOAc, separate layers
  5. extractionextract the aqu
  6. washlayer with EtOAc (3×), wash the combined organic layer with brine
  7. dry with materialdry with Na2SO4
  8. customRemove solvent and recrystallize residue from EtOAc/CyH 1+2

Sources & evidence

ORD record
ord-9c06d8a0afda4f07bcd84ed8c4dc599a
Source dataset
uspto-grants-2011_04
Patent number
US07923473B2

Reaction notes

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