Sodium Hydroxide → 5-Methyl-2-(1-methylcyclohexyl)-4-oxazoleacetic acid

HRID 746031Notes

Reaction equation

HRID 746031 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2([CH3:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[CH2:14][C:15]([O:17]CC1C=CC=CC=1)=[O:16].[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2([CH3:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53939088Benzyl 5-methyl-2-(1-methylcyclohexyl)-4-oxazoleacetate

Product 1

HCID 1460825-Methyl-2-(1-methylcyclohexyl)-4-oxazoleacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl 5-methyl-2-(1-methylcyclohexyl)-4-oxazoleacetate (1.0 g) was dissolved in ethanol (3 ml), and 2N sodium hydroxide (3 ml) was added. The mixture was heated on a water bath at 90° C. for 5 minutes, diluted with water and washed with ethyl ether. The aqueous layer was adjusted to pH 2 with hydrochloric acid and extracted with ethyl ether. The ethyl ether extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was recrystallized from hexane to give 5-methyl-2-(1-methylcyclohexyl)-4-oxazoleacetic acid as crystals; yield 0.41 g (56.9%). Mp 66°-67° C. The IR and NMR spectra of this product were in good agreement with those of the compound obtained in Example 15.

Workup

  1. washwashed with ethyl ether
  2. extractionextracted with ethyl ether
  3. extractionThe ethyl ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-94efbfe209704cd0a2c3277d4c59f698
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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