Hydrochloric Acid → [2-(2,2-Dimethylpropyl)-1,3-benzoxazol-5-yl]acetic acid

HRID 48150Notes

Reaction equation

HRID 48150 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:10][C:9]=2[CH:18]=1.[OH-].[Na+].Cl>CO.O>[CH3:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:19])=[O:2])=[CH:18][C:9]=2[N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22742087Methyl[(2,2-dimethylpropyl)benzoxazol-5yl]acetate

Product 1

HCID 22742085[2-(2,2-Dimethylpropyl)-1,3-benzoxazol-5-yl]acetic acidYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Methyl[(2,2-dimethylpropyl)benzoxazol-5-yl]acetate [from step 6] (5.00 g, 0.0185 mole) was dissolved in methanol (5 ml) and then a solution of sodium hydroxide (0.81 g, 0.0204 mole) in water (5 ml) was added slowly over 20 minutes, maintaining the temperature below 25° C. by external cooling. Once the addition was complete, the mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was poured slowly into water (50 ml) and concentrated hydrochloride acid was added until the pH of the mixture was below pH6. The mixture was stirred for 1 hour then filtered and the solid was washed thoroughly with water and dried. Trituration with hexane gave [(2,2-dimethylpropyl)benzoxazol-5yl]acetic acid (4.51 g) as a white solid, m.p. 108-109° C.

Workup

  1. temperaturemaintaining the temperature below 25° C. by external cooling
  2. additionOnce the addition
  3. additionwas added until the pH of the mixture
  4. stirringThe mixture was stirred for 1 hour
  5. filtrationthen filtered
  6. washthe solid was washed thoroughly with water
  7. customdried

Sources & evidence

ORD record
ord-3cdb97c1024243149817c1de919c0e7a
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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