Hydrochloric Acid → 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid

HRID 1264652Notes

Reaction equation

HRID 1264652 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([O:15]C)=[O:14])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][O:7][C:6]=2[CH:12]=1.[OH-].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][O:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18613659methyl 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylate

Product 1

HCID 112299388-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of intermediate (10) (0.25 mol) and potassium hydroxide (1 mol) in water (650 ml) was stirred and refluxed for 2 hours. The reaction mixture was cooled, acidified with HCl and the resulting precipitate was filtered off, washed with water, and dried, yielding 48 g of 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid (intermediate 11).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7296f04105dc4649b1763182a37a7321
Source dataset
uspto-grants-2003_04
Patent number
US06544997B1

Reaction notes

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