Lithium Hydroxide → 4-(3,4-Dichlorobenzyl)benzoic acid

HRID 2359323Notes

Reaction equation

HRID 2359323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58046347Ethyl 4-(3,4-dichlorobenzyl)benzoate

Product 1

HCID 580463204-(3,4-Dichlorobenzyl)benzoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 4-(3,4-dichlorobenzyl)benzoate (Preparation 170, 240 mg, 0.78 mmol) in THF/MeOH/water (4:3:2, 7.2 mL) was added lithium hydroxide (65 mg, 1.56 mmol) and the mixture was stirred at room temperature for 4 hours. The solvent was evaporated in vacuo and the residue acidified with 1M hydrochloric acid solution. The crude product was extracted with chloroform/methanol, and the extract dried over Na2SO4 and the solvent evaporated in vacuo to give the title compound as a white solid (160 mg, 73%)

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionThe crude product was extracted with chloroform/methanol
  3. dry with materialthe extract dried over Na2SO4
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-90d5ea67d1054be592ba63dc5e189222
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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