Water → HCID 15124011, compound

HRID 1084863Notes

Reaction equation

HRID 1084863 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][CH:10]=[C:9]([OH:17])[C:6]=2[C:7]=1[CH3:8])C.[OH-:18].[K+].[OH2:20]>>[CH3:8][C:7]1[C:6]2[C:9]([OH:17])=[CH:10][CH:11]=[C:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[C:5]=2[O:4][C:3]=1[C:1]([OH:20])=[O:18]

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20062763HCID 20062763, compound

Product 1

HCID 15124011HCID 15124011, compound

Procedure

Ethyl 3-methyl-4-hydroxy-7-tert-butylbenzofuran (0.405 g, 1.47 mmol) was saponified in a solution of KOH (0.247 g, 4.41 mmol) in refluxing water (10 mL) for two hours. Acidification of the cooled mixture led to precipitation of the product. 3-Methyl-4-hydroxy-7-tert-butylbenzofuran-2-carboxylic acid, compound 8, was collected by filtration and vacuum dried. This material was decarboxylated without further purification, mp 219°-222° C.; 1H NMR (DMSO-d6) d 1.38 (9H, s), 2.64 (3H, s), 6.55 (1H, d, J=8 Hz), 7.07 (1H, d, J=8 Hz), 9.66 (1H, s).

Workup

  1. customAcidification of the cooled mixture led to precipitation of the product
  2. filtration3-Methyl-4-hydroxy-7-tert-butylbenzofuran-2-carboxylic acid, compound 8, was collected by filtration and vacuum
  3. customdried
  4. customThis material was decarboxylated without further purification, mp 219°-222° C.

Sources & evidence

ORD record
ord-f4d485a1310240c292095d0177552156
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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