Hydrochloric Acid → [4-(2-Methyl-pyridin-4-yl)-phenyl]-acetic acid

HRID 592131

Reaction equation

HRID 592131 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-].Cl>C1COCC1.CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58447956Ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate

Product 1

HCID 58447644[4-(2-Methyl-pyridin-4-yl)-phenyl]-acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 (1.81 g, 7.1 mmol), LiOH (0.17 g, 7.1 mmol) in THF (30 mL), methanol (10 mL) and H2O (10 mL) was stirred at 60° C. for 1 hour. After cooled down to 0° C., the mixture was neutralized with 1 N HCl at 0° C. and then taken to dryness by rotary evaporation to yield 2-(4-(2-methylpyridin-4-yl)phenyl)acetic acid 26-3. The product was used for next step without further purification. MS m/z 228.1 (M+1).

Workup

  1. temperatureAfter cooled down to 0° C.
  2. customtaken to dryness by rotary evaporation

Sources & evidence

ORD record
ord-3cd968b6de61405b88017c14e0212e96
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Linked notes

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