Sodium Hydroxide → (2,6-Diethyl-4-methylphenyl)glyoxylic acid

HRID 571619Notes

Reaction equation

HRID 571619 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:18])[C:13]([O:15]CC)=[O:14])[CH3:2].[OH-].[Na+]>O1CCCC1>[CH2:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:12](=[O:18])[C:13]([OH:15])=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56942718Ethyl (2,6-diethyl-4-methylphenyl)glyoxylate

Product 1

HCID 56942555(2,6-Diethyl-4-methylphenyl)glyoxylic acidYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2,6-diethyl-4-methylphenyl)glyoxylate (320.82 g) in tetrahydrofuran (600 ml) was added 10.7 weight % of aqueous sodium hydroxide solution (900 ml) dropwise at 10° C. of the internal temperature over 2 hours. The resulting mixture was stirred at room temperature for 1 hour. Then, the organic layer was evaporated, and the aqueous layer was washed with tert-butyl methyl ether. To the aqueous layer was added concentrated hydrochloric acid (180 ml) dropwise, and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure to give 166.55 g of (2,6-diethyl-4-methylphenyl)glyoxylic acid.

Workup

  1. customThen, the organic layer was evaporated
  2. washthe aqueous layer was washed with tert-butyl methyl ether
  3. additionTo the aqueous layer was added concentrated hydrochloric acid (180 ml) dropwise
  4. extractionextracted with tert-butyl methyl ether
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ab08890f4244a24bbf62db26e8406e8
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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