Lithium Hydroxide → 4-[(3,4-Dichlorophenyl)methoxy]benzoic acid

HRID 508418Notes

Reaction equation

HRID 508418 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=1.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 2764515HCID 2764515, compound

Product 1

HCID 27644494-[(3,4-Dichlorophenyl)methoxy]benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(3,4-dichlorobenzyl)oxy]benzoate (Preparation 8, 750 mg; 2.41 mmol) in tetrahydrofuran (12 mL) was added an aqueous solution of lithium hydroxide (2 M, 6 mL, 12 mmol) and the reaction stirred at reflux for 4 hours. Upon consumption of starting material the reaction mixture cooled to room temperature and solvent removed in vacuo. The resulting residue was dissolved in water (15 mL) and acidified with 2M hydrochloric acid solution. The aqueous phase was then extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over magnesium sulphate, filtered and evaporated in vacuo to give the title compound (620 mg, 87%) as a white solid.

Workup

  1. temperatureat reflux for 4 hours
  2. customUpon consumption of starting material the reaction mixture
  3. customsolvent removed in vacuo
  4. dissolutionThe resulting residue was dissolved in water (15 mL)
  5. extractionThe aqueous phase was then extracted with dichloromethane (3×25 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e008e5bb5523408083b6d856edff6c48
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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