Sodium Hydroxide → (2-(1-Naphthyl)-6-benzoxazolyl)acetic acid

HRID 1372751Notes

Reaction equation

HRID 1372751 reaction equation
[C:1]1([C:11]2[O:12][C:13]3[CH:19]=[C:18]([CH2:20][C:21]([O:23]C)=[O:22])[CH:17]=[CH:16][C:14]=3[N:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1>[C:1]1([C:11]2[O:12][C:13]3[CH:19]=[C:18]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:16][C:14]=3[N:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778440Methyl (2-(1-naphthyl)-6-benzoxazolyl)acetate

Product 1

HCID 17858916(2-(1-Naphthyl)-6-benzoxazolyl)acetic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl (2-(1-naphthyl)-6-benzoxazolyl)acetate (223 mg, 0.70 mmol) were added THF (4 ml) and 0.5N NaOH (4.2 ml, 2.10 mmol). The resulting mixture was stirred at room temperature for 2 days. The reaction mixture was acidified 15 with ice-1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (2-(1-naphthyl)-6-benzoxazolyl)acetic acid (194 mg, 91%) as a pale yellow solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb4ffed30c48460d88f71ae4f4eb9e64
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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