4-METHOXYBENZOIN → 3-[4-(4-Methoxyphenyl)-5-phenyl-1,3-oxazol-2-yl]propanoic acid

HRID 542882Notes

Reaction equation

HRID 542882 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=O)=[CH:5][CH:4]=1.[C:19]1(=O)[O:24][C:22](=[O:23])[CH2:21][CH2:20]1.C([N:28](CC)CC)C.C([O-])(=O)C.[NH4+]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:28]=[C:19]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[O:12][C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 37914-METHOXYBENZOINHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 517165Ammonium Acetate

Product 1

HCID 189565763-[4-(4-Methoxyphenyl)-5-phenyl-1,3-oxazol-2-yl]propanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

4-Methoxybenzoin (24 g, 0.1 m) prepared according to B. R. Kinney, J.A.C.S., 51, 1595 (1929), succinic anhydride (12 g, 0.12 m), triethylamine (5 ml, 0.035 m) and toluene (30 ml) were heated on a steam cone for three hours under nitrogen. After cooling, acetic acid (60 ml) and ammonium acetate (10.5 g) were added and heating was resumed as 60 ml of solvent were distilled. Acetic acid (30 ml) was added and 30 ml of solvent were distilled. The previous step was repeated twice more. The mixture was cooled and poured into 600 ml of ice water, decanted, triturated twice with ice water and filtered. Recrystallization from 50% aqueous methanol gave 24.2 g, (71%) of 4-(4-methoxyphenyl-5-phenyl-2-oxazolepropanoic acid, m.p. 118°-120° C.

Workup

  1. temperatureAfter cooling
  2. temperatureheating
  3. distillationwere distilled
  4. additionAcetic acid (30 ml) was added
  5. distillation30 ml of solvent were distilled
  6. temperatureThe mixture was cooled
  7. additionpoured into 600 ml of ice water
  8. customdecanted
  9. customtriturated twice with ice water
  10. filtrationfiltered
  11. customRecrystallization from 50% aqueous methanol

Sources & evidence

ORD record
ord-9058a30d08104374a0f88e9776e42424
Source dataset
uspto-grants-1987_04
Patent number
US04659728

Reaction notes

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