Hydrochloric Acid → 5-(2-Methoxyethoxy)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845278Notes

Reaction equation

HRID 1845278 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:19]([O:21]C)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:19]([OH:21])=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58188233Methyl 5-(2-methoxyethoxy)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581879975-(2-Methoxyethoxy)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-(2-methoxyethoxy)-4′-methylbiphenyl-3-carboxylate (703 mg, 2.34 mmol) in tetrahydrofuran (40 mL) was added 2.5 M aqueous lithium hydroxide solution (9.6 mL, 24 mmol). After being stirred at room temperature overnight, the mixture was acidified to pH=5 by addition of 2N HCl and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to afford the title compound. 1H NMR (CD3OD, 400 MHz): 7.84 (t, 1H, J=1.6 Hz), 7.55-7.51 (m, 3H), 7.34 (t, 1H, J=2.0 Hz), 7.27 (d, 2H, J=8.0 Hz), 4.22 (m, 2H), 3.79 (m, 2H), 3.45 (s, 3H), 2.38 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9e9bc5809d394db3821e29859a5eeb1d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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