Sodium Hydroxide → 5-Acetyl-2-(benzyloxy)benzoic acid

HRID 421045Notes

Reaction equation

HRID 421045 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>CO.O1CCCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([CH:9]=1)[C:3]([OH:21])=[O:2])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12368981Benzoic acid, 5-acetyl-2-(phenylmethoxy)-, methyl ester

Product 1

HCID 218806135-Acetyl-2-(benzyloxy)benzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Acetyl-2-benzyloxybenzoic acid methyl ester (5.69 g, 20 mmol) was dissolved in a mixed solvent of methanol (20 mL) and tetrahydrofuran (20 mL). 2 N sodium hydroxide (11 mL) was added dropwise, and the mixture was stirred for 8 hours. The solvent was evaporated under reduced pressure. 2 N hydrochloric acid was added to the residue, and it was extracted with dichloromethane. After the dichloromethane layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated, the residue was washed with isopropyl ether to give the title compound (4.92 g, 91.0%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. addition2 N hydrochloric acid was added to the residue, and it
  3. extractionwas extracted with dichloromethane
  4. washAfter the dichloromethane layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washthe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-a8a6c30e223b40ae96c8ac2c594708f4
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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