Hydrochloric Acid → HCID 12525867, compound

HRID 441668Notes

Reaction equation

HRID 441668 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:10](=[O:11])[O:9][CH2:8]2)([O:3]C)=[O:2].C[O-].[Na+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.Cl>CO.O>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][CH2:8][C:7]1[CH:6]=[C:5]([C:1]([OH:3])=[O:2])[CH:14]=[CH:13][C:12]=1[C:10]([OH:9])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67970o-FluorobenzaldehydeHCID 10942334Sodium MethoxideHCID 23299433Methyl 1-oxo-1,3-dihydro-2-benzofuran-5-carboxylate

Product 1

HCID 12525867HCID 12525867, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8.5 G. of 5-carbomethoxyphthalide and 2.43 g. of sodium methoxide were refluxed for 15 minutes in 250 ml of methanol, and then 5.55 g. of o-fluorobenzaldehyde was added. The mixture was refluxed for 20 hours and then poured into water and acidified with dilute hydrochloric acid. The solution was extracted with ethyl acetate and the extract washed, dried and evaporated. The residue was refluxed for 48 hours in 75 ml of acetic acid and 45 ml of 57% aqueous hydriodic acid containing 7.5 g. of red phosphorus. The mixture was poured into water and filtered. The residue was dissolved in ethanol and the solution filtered and evaporated to afford 2-(o-fluorophenethyl)benzene-1,4-dicarboxylic acid which was cyclized according to the method described in Example I, A to obtain 2-carboxy-9-fluoro-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene having a m.p. of 248.5° to 249.5° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract washed
  4. customdried
  5. customevaporated
  6. temperatureThe residue was refluxed for 48 hours in 75 ml of acetic acid
  7. additionThe mixture was poured into water
  8. filtrationfiltered
  9. dissolutionThe residue was dissolved in ethanol
  10. filtrationthe solution filtered
  11. customevaporated

Sources & evidence

ORD record
ord-7e40f12802874dbd9121ec747b51adc0
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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