Sodium Hydroxide → 4-(Benzyloxy)-3-methoxybenzoic acid

HRID 1576913Notes

Reaction equation

HRID 1576913 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]=[O:9]>[Ag]=O.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:8]([OH:1])=[O:9])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Product 1

HCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide (12g.; 0.3m) was dissolved in 200 ml. of water, silver oxide (11.6g.; 0.05m) added and the resulting mixture warmed to 50°C, 3-methoxy-4-benzyloxybenzaldehyde (12.1g; 0.05m) added in one portion and the mixture heated to 60°C with stirring for 1 hour, stirred 18 hours at room temperature, filtered and acidified to give the acid which was recrystallised from glacial acetic acid, m.p. 172°-3°C.

Workup

  1. temperaturethe mixture heated to 60°C
  2. stirringstirred 18 hours at room temperature
  3. filtrationfiltered
  4. customto give the acid which
  5. customwas recrystallised from glacial acetic acid, m.p. 172°-3°C.

Sources & evidence

ORD record
ord-fd9a4a330e5b40adb18c67374aaf6ec6
Source dataset
uspto-grants-1976_09
Patent number
US03983164

Reaction notes

Loading…