Benzaldehyde → Bis-benzyloxy benzoic acid

HRID 2291655Notes

Reaction equation

HRID 2291655 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:25][Mn](=O)(=O)=O.[K+].C(=O)C1C=CC=CC=1>CC(C)=O.O>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]([OH:25])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 516875Potassium Permanganate2×HCID 10870855Dibenzyloxybenzaldehyde

Product 1

HCID 10520703Bis-benzyloxy benzoic acidYield 212.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

19.8 g of 2,3-dibenzyloxybenzaldehyde are dissolved in 100 ml of acetone. While stirring vigorously and heating at 40° C., a solution of 4.0 g of KMnO4 in 90 ml of H2O is added within 45 min, the precipitated benzaldehyde being redissolved by the addition of a total of 150 ml of acetone. Once addition of the KMnO4 solution is complete, the mixture is boiled under reflux for one hour. The hot solution is then filtered, and the precipitate is washed with hot water. The carboxylic acid crystallizes out in fine white needles on acidification of the cold aqueous solution with dilute HCl. 18.0 g of the desired compound are obtained (92% yield). MS: 334 (M+); M.p.: 185°-187° C.

Workup

  1. temperatureunder reflux for one hour
  2. filtrationThe hot solution is then filtered
  3. washthe precipitate is washed with hot water
  4. customThe carboxylic acid crystallizes out in fine white needles on acidification of the cold aqueous solution with dilute HCl

Sources & evidence

ORD record
ord-457c9fec9c2b439394cbdcc3e4cb0fea
Source dataset
uspto-grants-1989_01
Patent number
US04797471

Reaction notes

Loading…