Hydrochloric Acid → 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid

HRID 383587

Reaction equation

HRID 383587 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=2[O:21][CH3:22])[CH:8]=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-].Cl>CC#N>[CH3:22][O:21][C:12]1[C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 161162902',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 160407182',3',4'-Trimethoxy-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 2′,3′,4′-Trimethoxy-biphenyl-3-carboxylic acid methyl ester (43) (566 mg, 1.87 mmol) in MeCN (19.0 mL) at rt and add 1M aqu LiOH (9.36 mL, 9.36 mmol). Stir reaction mixture overnight at rt. Quench reaction mixture (cooling bath) with 1M aqu. HCl (to get pH ca. 3). Extract the mixture with EtOAc (3×), wash the combined organic layer with brine and dry with Na2SO4. Recrystallize crude product from EtOAc/CyH 1+3 to obtain 2′,3′,4′-Trimethoxy-biphenyl-3-carboxylic acid (44) as a white solid (392 mg, to 72%). 1H NMR (400 MHz, CD3OD: 3.68 (s, 3H); 3.93 (br.s, 6H); 6.92 (d, 1H, J=8.6 Hz); 7.11 (d, 1H, J=8.6 Hz); 7.54 (t, 1H, J=7.7 Hz); 7.75 (d, 1H, J=7.6 Hz); 8.01 (d, 1H, J=7.8 Hz); 8.18 (br.s 1H).

Workup

  1. customreaction mixture overnight at rt
  2. customQuench
  3. customreaction mixture (cooling bath) with 1M aqu
  4. extractionExtract the mixture with EtOAc (3×)
  5. washwash the combined organic layer with brine
  6. dry with materialdry with Na2SO4
  7. customRecrystallize crude product from EtOAc/CyH 1+3

Sources & evidence

ORD record
ord-dc7bc1aef68a48c3bfee2aad880a3c97
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Linked notes

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