Sodium Hydroxide → (2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 38705Notes

Reaction equation

HRID 38705 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][O:24]C(=O)C)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[OH-].[Na+]>C1COCC1.CO>[OH:24][CH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:13]=1[C:7]1[C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:28])=[O:2])[CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67429487(2'-Acetoxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 45280409(2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (2′-acetoxymethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.54 mmol) in THF (1 mL) and MeOH (0.8 mL) was added 1N aqueous NaOH (0.6 mL), and the reaction was stirred at room temperature for 1.5 hours. The mixture was partitioned between CH2Cl2 and aqueous HCl, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and aqueous HCl
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a3dd2075bc3497ca2c1fd02133ef234
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Reaction notes

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