Hydrochloric Acid → HCID 69666585, compound

HRID 1791052Notes

Reaction equation

HRID 1791052 reaction equation
[OH-].[K+].[Cl:3][CH:4]=[C:5]1[CH:11]=[CH:10][C:9]2[CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=[CH:15][C:8]=2[O:7][CH2:6]1.Cl>C(O)C>[Cl:3][CH:4]=[C:5]1[CH:11]=[CH:10][C:9]2[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:8]=2[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69667024Methyl 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate

Product 1

HCID 69666585HCID 69666585, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

145 mg (2.6 mmol) of potassium hydroxide pellets are added to 0.5 g (2 mmol) of methyl 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 32, in solution in 8 ml of 80% aqueous ethanol, and the medium is brought to reflux for 3 hours. After cooling, the medium is brought to acidity by addition of 1N hydrochloric acid. The precipitate is filtered off and then washed with diisopropyl ether to provide 300 mg (63%) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylic acid in the form of a white solid comprising two Z/E isomers as a mixture in an 85/15 ratio; M.p.>260° C.

Workup

  1. customprepared
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationThe precipitate is filtered off
  5. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-ec588e9c9ad0476aa2ef0f51fdd2c601
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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