Acetic Acid → 15023-39-9

HRID 862153Notes

Reaction equation

HRID 862153 reaction equation
S(N)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=O)=O.C[C:13]([OH:15])=[O:14]>[Zn]>[C:4]12([C:13]([OH:15])=[O:14])[CH2:8][CH:7]([CH2:9][CH2:10]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6269P-Toluenesulfonamide

Product 1

HCID 1785159515023-39-9Yield 96.8%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Compound 4 (27.0 g; 0.062 mole) and Zn° (16.2 g; 0.249 mol) were combined in HOAc (100 ml) and heated to reflux for one half hour. The reaction mixture was cooled and filtered through Celite®. The filtrate was concentrated and the residue suspended in H2O, whereupon the oil crystallized. The solid was filtered, washed with H2O and suction dried to yield 18.4 g (96.8%) of Compound 5 as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for one half hour
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite®
  5. concentrationThe filtrate was concentrated
  6. customcrystallized
  7. filtrationThe solid was filtered
  8. washwashed with H2O and suction
  9. customdried

Sources & evidence

ORD record
ord-5aaf6fbb067a4696a20714f22d8c8f12
Source dataset
uspto-grants-1998_02
Patent number
US05717098

Reaction notes

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