Sodium Hydroxide → 3-(Benzyloxy)-5-methoxybenzoic acid

HRID 38656Notes

Reaction equation

HRID 38656 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12658782Methyl 3-(benzyloxy)-5-methoxybenzoate

Product 1

HCID 126587813-(Benzyloxy)-5-methoxybenzoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.45 g (0.0174 mmol) of methyl 3-(benzyloxy)-5-methoxybenzoate (161) was suspended in 120 mL of 95% ethanol and 5 mL water. An amount of 2.00 g (0.05 mmol) of sodium hydroxide was added. The mixture was heated at reflux for 1 h. After the mixture was evaporated, the residue was quenched with 150 mL of water. The solution was neutralized with dil aq HCl and then the precipitate was collected and washed with water and acetone to give 162.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. customAfter the mixture was evaporated
  4. customthe residue was quenched with 150 mL of water
  5. customthe precipitate was collected
  6. washwashed with water and acetone

Sources & evidence

ORD record
ord-b7cce4cbf9a24832b82a74bb5d1139c9
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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