Sodium Hydroxide → HCID 18329461, compound

HRID 1250087Notes

Reaction equation

HRID 1250087 reaction equation
[CH:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]1[O:13]CC(C)(C)N=1)([CH3:3])[CH3:2].[OH-:19].[Na+]>S(=O)(=O)(O)O>[CH:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12]([OH:13])=[O:19])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10243704HCID 10243704, compound

Product 1

HCID 18329461HCID 18329461, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-(2-isopropyl-3-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (6.18 g, 25 mmol) in 35% solution of sulfuric acid (40 mL) was stirred at reflux for 48 hours. Upon cooling, solid sodium hydroxide (18.15 g) was slowly added. The reaction mixture was extracted with diethyl ether, and the combined organic extracts were extracted with sodium bicarbonate solution. The bicarbonate extracts were then acidified with 3N hydrochloric acid, filtered and dried to give 2-isopropyl-3-methoxybenzoic acid as a white crystalline solid (1.73 g, 35.7%).

Workup

  1. temperatureat reflux for 48 hours
  2. temperatureUpon cooling
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. extractionthe combined organic extracts were extracted with sodium bicarbonate solution
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-3ad4948b116840b2937f37c82abe7cd7
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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