Hydrochloric Acid → 3-Methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acid

HRID 1791046Notes

Reaction equation

HRID 1791046 reaction equation
[OH-].[K+].[CH2:3]=[C:4]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[CH:13]=[CH:14][C:7]=2[O:6][CH2:5]1.Cl>C(O)C>[CH2:3]=[C:4]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22042256HCID 22042256, compound

Product 1

HCID 220422573-Methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g of potassium hydroxide pellets are added to 4 g (18.5 mmol) of methyl 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 35, in solution in 20 ml of 80% aqueous ethanol. The medium is brought to reflux for 4 hours and then, after cooling, is treated with 1N hydrochloric acid until precipitation. The solid is filtered off and dried to give 3.3 g (88%) of 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acid in the form of a white solid; M.p.=188° C.

Workup

  1. customprepared
  2. temperatureto reflux for 4 hours
  3. temperatureafter cooling
  4. filtrationThe solid is filtered off
  5. customdried

Sources & evidence

ORD record
ord-4ac67eff34a54ca7bf3f8d6b1731f03d
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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