HCID 12689097, compound → HCID 12689101, compound

HRID 1659484Notes

Reaction equation

HRID 1659484 reaction equation
[C:1]([C:9]12[O:15]C1[O:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]2=[O:21])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O.O>[OH:15][C:9]1[C:10](=[O:21])[CH:11]=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13][C:1]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12689097HCID 12689097, compound

Product 1

HCID 12689101HCID 12689101, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 6-benzoyl-5-oxo-2,7-dioxabicyclo[4.1.0]hept-3-ene-3-carboxylate (3.5 g) in 98-100% formic acid (50 ml) was heated under reflux for 11/2 hours, cooled, diluted with water and extracted with ethyl acetate. The extract was washed with excess sodium bicarbonate solution, dried and evaporated and the solid residue was crystallised twice from chloroform-petroleum ether 60°-80° C. to give the title product (mp 155°-157° C.).

Workup

  1. temperatureunder reflux for 11/2 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with excess sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customthe solid residue was crystallised twice from chloroform-petroleum ether 60°-80° C.

Sources & evidence

ORD record
ord-7988a1725e9d42889790f271e3a81a3d
Source dataset
uspto-grants-1981_12
Patent number
US04304728

Reaction notes

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