P-Toluic Acid → 4-Methylbenzaldehyde

HRID 1357348Notes

Reaction equation

HRID 1357348 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](O)=[O:9])=[CH:6][CH:7]=1.C1(C)C(C([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=O)=CC=CC=1>>[C:2]1([CH3:1])[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][OH:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 7470P-Toluic AcidHCID 85949731HCID 85949731, compound

Product 2

HCID 77254-MethylbenzaldehydeHCID 115054-Methylbenzyl alcohol

Conditions

Temperature
90 °C

Procedure

To 2100 g of the reaction filtrate obtained in the same condition as of the Example 1, 364.0 g of aqueous sodium hydroxide solution (sodium hydroxide was 1.5 times in mole with respect to a total amount of the p-toluic acid and p-methylbenzyl toluate) was added, stirred at 90° C. for 4 hours, and after standing still 15 minutes, the solution was separated into 1937.5 g of organic layer and 372.0 g of water layer. To said organic layer, 0.27 g of aqueous 40% NaOH solution (sodium hydroxide was 0.11% with respect to total amount of the p-tolualdehyde and p-methylbenzyl alcohol contained in the solution) was added, and distilled to obtain 82.2 g of p-tolualdehyde, and 84.8 g of p-methylbenzyl alcohol. As the result of the analysis by gas chromatography, purities of the p-tolualdehyde and p-methylbenzyl alcohol were found as 99.3% and 99.5%, respectively.

Workup

  1. additionwas added
  2. waitafter standing still 15 minutes
  3. customthe solution was separated into 1937.5 g of organic layer and 372.0 g of water layer
  4. additionwas added
  5. distillationdistilled

Sources & evidence

ORD record
ord-698d8e5dcc4744f99a6acf22f866d859
Source dataset
uspto-grants-2003_07
Patent number
US06590129B2

Reaction notes

Loading…