Hydrochloric Acid → 4-(1-Ethoxyethyl)benzoic acid

HRID 2170473Notes

Reaction equation

HRID 2170473 reaction equation
[CH2:1]([O:3][CH:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)[CH3:5])[CH3:2].[OH-].[Li+].Cl>CO.O>[CH2:1]([O:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)[CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89580551Methyl 4-(1-ethoxyethyl)benzoate

Product 1

HCID 189137424-(1-Ethoxyethyl)benzoic acidYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the solution of methyl 4-(1-ethoxyethyl)benzoate (191 mg, 0.92 mmol) in methanol and water (50 mL/10 mL) was added lithium hydroxide (100 mg, 4.2 mmol), the solution was stirred at room temperature for 12 hours. Then the solution was acidified by hydrogen chloride (1 N/mol) pH to 6, extracted with dichloromethane (80 mL*3), evaporated the solvent to give 4-(1-ethoxyethyl)benzoic acid (167 mg, 93%).

Workup

  1. extractionto 6, extracted with dichloromethane (80 mL*3)
  2. customevaporated the solvent

Sources & evidence

ORD record
ord-14fc3b6f7a22478282c172e23675d490
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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