Potassium Hydroxide → HCID 15124012, compound

HRID 1084864Notes

Reaction equation

HRID 1084864 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:19])=[C:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]=2[O:4][C:3]=1[C:20]([O:22]CC)=[O:21].[OH-].[K+]>O.CO>[CH3:1][C:2]1[C:6]2[C:7]([OH:19])=[C:8]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:9]=[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:5]=2[O:4][C:3]=1[C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15124009HCID 15124009, compound

Product 1

HCID 15124012HCID 15124012, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 3-methyl-4-hydroxy-5,7-di-tert-butylbenzofuran-2-carboxylate (0.475 g, 1.43 mmol) was refluxed in a solution of KOH (0.241 g, 4.29 mmol) in water (10 mL) and methanol (2 mL) for two hours. Acidification of the cooled mixture led to precipitation of the product. 3-Methyl-4-hydroxy-5,7-di-tert-butylbenzofuran-2-carboxylic acid, compound 9, was collected by filtration and vacuum dried. This material was decarboxylated without further purification. mp 241°-243° C.; 1H NMR (DMSO-d6) d 1.40 (18H, s), 2.71 (3H, s), 7.18 (1H, s), 8.35 (1H, s).

Workup

  1. customAcidification of the cooled mixture led to precipitation of the product
  2. filtration3-Methyl-4-hydroxy-5,7-di-tert-butylbenzofuran-2-carboxylic acid, compound 9, was collected by filtration and vacuum
  3. customdried
  4. customThis material was decarboxylated without further purification

Sources & evidence

ORD record
ord-d658179b0344407595c667e4fd28fcec
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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