Succinic anhydride → HCID 20207520, compound

HRID 542879Notes

Reaction equation

HRID 542879 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]([OH:16])[C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:19]1(=O)[O:24][C:22](=[O:23])[CH2:21][CH2:20]1.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.C([O-])(=O)C.[NH4+:46]>C(O)(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]2[O:16][C:19]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:46][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 7922Succinic anhydrideHCID 8400BenzoinHCID 517165Ammonium AcetateHCID 12505004HCID 12505004, compound

Product 1

HCID 20207520HCID 20207520, compoundYield 96.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4'-Methoxybenzoin (17.4 g, 0.0716 m) prepared according to R. T. Arnold and R. C. Fuson, J.A.C.S., 58, 1295 (1936), succinic anhydride (8.7 g, 0.086 m), triethylamine (3.541, 0.025 m) and toluene (30 ml) were heated on a steam cone under nitrogen for 2.5 hours. Thin layer chromatography (silica gel 60, ethyl acetate) showed complete conversion of the starting benzoin. Glacial acetic acid (40 ml) and ammonium acetate (7.6 g) were added and 40 ml of solvent were removed by distillation over 1 hour. Glacial acetic acid (40 ml) was added and 40 ml solvent removed by distillation. Glacial acetic acid (40 ml) was added and again 40 ml solvent removed by distillation. The cooled mixture was poured into 600 ml of ice water and the solid product was filtered. The product was purified by chromatography on a silica gel column using gradient elution from 100% chloroform to 90% chloroform:10% ethylacetate. Crystallization of the residue (29 g) from 200 ml of 50% aq. methanol gave 22.5 g of 5-(4-methoxyphenyl)-4-phenyl-2-oxazolepropanoic acid, m.p. 123°-126° C.

Workup

  1. custom40 ml of solvent were removed by distillation over 1 hour
  2. additionGlacial acetic acid (40 ml) was added
  3. custom40 ml solvent removed by distillation
  4. additionGlacial acetic acid (40 ml) was added
  5. customagain 40 ml solvent removed by distillation
  6. additionThe cooled mixture was poured into 600 ml of ice water
  7. filtrationthe solid product was filtered
  8. customThe product was purified by chromatography on a silica gel column
  9. washelution from 100% chloroform to 90% chloroform
  10. customCrystallization of the residue (29 g) from 200 ml of 50% aq. methanol

Sources & evidence

ORD record
ord-acac3c9fc0264459a1a0a00be32cc26c
Source dataset
uspto-grants-1987_04
Patent number
US04659728

Reaction notes

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