Hydrochloric Acid → 6-(tert-Butoxycarbonyl)-1-benzofuran-2-carboxylic acid

HRID 339110Notes

Reaction equation

HRID 339110 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:17]([O:19]CC)=[O:18].[OH-].[Na+].Cl>C(O)C>[C:13]([O:12][C:10]([C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[C:2]([C:17]([OH:19])=[O:18])[O:1][C:5]=2[CH:6]=1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 582479886-tert-Butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate

Product 1

HCID 582479766-(tert-Butoxycarbonyl)-1-benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-tert-butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate (490 mg, 1.68 mmol) in ethanol (15 ml) was admixed with sodium hydroxide solution (3.36 ml, 1 M) and heated under reflux for 2 h. The cooled solution was added to ice-cooled hydrochloric acid (1 M), and the precipitate was filtered off with suction, washed with a little water and dried under reduced pressure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. additionThe cooled solution was added to ice-
  4. filtrationthe precipitate was filtered off with suction
  5. washwashed with a little water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-521f464229ee40adae78b6fdb1fa9772
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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