HCID 12689097, compound → HCID 12689101, compound

HRID 544160Notes

Reaction equation

HRID 544160 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-8c22644fb0814ae39fd97d12069e5ced
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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