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

HRID 579217Notes

Reaction equation

HRID 579217 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 3 L volume four-necked flask, ethyl 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetate (9-a) (320.82 g) and tetrahydrofuran (600 ml) were added at room temperature and cooled. 10.7% by weight of aqueous sodium hydroxide solution (900 ml) was added dropwise at 10° C. over 2 hours. The resulting mixture was stirred at room temperature for 1 hour. After the organic solvent was removed under reduced pressure, tert-butyl methyl ether was added to the aqueous layer to wash. After the organic layer was removed, to the aqueous layer was added dropwise concentrated hydrochloric acid (180 ml), and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure to give 166.55 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetic acid (8-a).

Workup

  1. temperaturecooled
  2. customAfter the organic solvent was removed under reduced pressure, tert-butyl methyl ether
  3. additionwas added to the aqueous layer
  4. washto wash
  5. customAfter the organic layer was removed, to the aqueous layer
  6. additionwas added dropwise concentrated hydrochloric acid (180 ml)
  7. extractionextracted with tert-butyl methyl ether
  8. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-23e01e95bf0a4876a9a78c670723f063
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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