Acetic Acid → HCID 21439773, compound

HRID 1579515Notes

Reaction equation

HRID 1579515 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]([OH:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][OH:15])=[CH:5][CH:4]=1.C(O)(=O)C.[Se](=O)=O>CC(O)C>[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[O:15])(=[O:16])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24007Selenium DioxideHCID 10800331HCID 10800331, compound

Product 1

HCID 21439773HCID 21439773, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 26 g. of 4'-methoxy-2-hydroxymethylbenzhydrol in 140 ml. of acetic acid and 14.5 g. selenium dioxide was refluxed for 2 hours. The mixture was filtered and the filtrate was made basic. An oil separated which crystallized on standing and was collected. Recrystallization from a mixture of methylene chloride and petroleum ether gave off-white platelets melting at 90°-91°. Ultraviolet maxima (2-propanol) at 221 mμ (ε = 21,600), 258 mμ (ε = 12,400) and 292 mμ (ε = 17,000); infrared absorption (CHCl3) at 1660 cm-1 and at 1700 cm-1.

Workup

  1. filtrationThe mixture was filtered
  2. customAn oil separated which
  3. customcrystallized
  4. customwas collected
  5. customRecrystallization
  6. additionfrom a mixture of methylene chloride and petroleum ether
  7. customgave off-white platelets melting at 90°-91°
  8. custominfrared absorption (CHCl3) at 1660 cm-1

Sources & evidence

ORD record
ord-68b77290a1a244dd8b0562d3467faf71
Source dataset
uspto-grants-1976_01
Patent number
US03931217

Reaction notes

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