Sodium Hydroxide → 3-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-phenol

HRID 1994075Notes

Reaction equation

HRID 1994075 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([O:21]C(=O)C)[CH:18]=[CH:19][CH:20]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68677549Acetic acid 3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl ester

Product 1

HCID 686778803-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the title A compound, acetic acid 3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl ester (3.92 g, 12.14 mmol) in methanol (15 mL) is added sodium hydroxide (0.97 g, 24.27 mmol) in water (15 mL) at RT. The reaction mixture is stirred for 4 h. The reaction mixture is concentrated at reduced pressure, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenol as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated at reduced pressure
  2. additionpoured into water
  3. customthe aqueous layer is separated
  4. washwashed with ethyl acetate twice
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined ethyl acetate extract
  7. dry with materialis dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9868992d089540128196abbcfb30ac5a
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

Loading…