Sodium Hydroxide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 1630966Notes

Reaction equation

HRID 1630966 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[OH-].[Na+]>CCO>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58554139Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (40.0 g, 148 mmol) in EtOH (1.2 L) at RT was treated with a 5N aqueous solution of NaOH (90 mL, 450 mmol). The reaction mixture was stirred at 60° C. for 1 hour, and then concentrated under reduced pressure. The yellow solid was taken up with water (800 mL) and washed twice with EtOAc. The aqueous layer was acidified with a concentrated aqueous solution of HCl until pH=2 and was extracted with EtOAc (2×400 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated affording the title compound as a yellow solid (35.1 g, 92%). HPLC (Method A), Rt 4.5 min (Purity: 96.4%). UPLC/MS, M−(ESI): 255.2. 1H NMR (DMSO-d6, 300 MHz) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.91 (m, 1H), 7.33-7.22 (m, 4H), 7.09 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed twice with EtOAc
  3. extractionwas extracted with EtOAc (2×400 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5430dcd2aa6640c192e65ed2d0c0ab20
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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