Sodium Hydroxide → 4-(Benzyloxy)benzoic acid

HRID 1500992Notes

Reaction equation

HRID 1500992 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 299810Methyl 4-(benzyloxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydroxide (1.80 g, 45 mmol) was added to a solution of methyl 4-(benzyloxy)benzoate (2.18 g, 9 mmol) in methanol (5 mL) and water (10 mL). The reaction mixture was stirred at 65° C. for 3 hours. After the reaction, the solvent was removed in vacuo. 3N hydrochloric acid was added to make pH 2, and the product was extracted with dichloromethane (100 mL×3). The combined organics phase was washed with brine (20 mL×3), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to give 4-(benzyloxy)benzoic acid (1.95 g, 95%). LRMS (M+H+) m/z: calcd 227.08. found 227.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. addition3N hydrochloric acid was added
  4. extractionthe product was extracted with dichloromethane (100 mL×3)
  5. washThe combined organics phase was washed with brine (20 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-9bd39c9104e1409fb98c2453676ab5e8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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