Sodium Acetate → HCID 12677753, compound

HRID 2419469Notes

Reaction equation

HRID 2419469 reaction equation
[B](F)F.[C:4]([CH:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH2:8]1)(=[O:6])[CH3:5].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:4]([CH:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH2:8]1)(=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 86735231HCID 86735231, compound

Product 1

HCID 12677753HCID 12677753, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-acetyl-4-chromanone boron difluoride complex (13 g, 54.5 mmoles, described in Example 4) and anhydrous sodium acetate (52 g) in glacial acetic acid (235 ml) is heated on a steam bath for one hr. The solution is poured on ice and the resulting mixture is extracted with ether. The organic extract is washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution, dried and evaporated. The residue is subjected to chromatography on silica gel using benzene-hexane (1:1) as eluant. Evaporation of the eluate gives the title compound, m.p. 73°-74° C, νmaxCHCl 3 1600 cm-1.

Workup

  1. additionThe solution is poured on ice
  2. extractionthe resulting mixture is extracted with ether
  3. extractionThe organic extract
  4. washis washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customEvaporation of the eluate

Sources & evidence

ORD record
ord-4878015763304d6b8083a83a0d2437ea
Source dataset
uspto-grants-1978_08
Patent number
US04105778

Reaction notes

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