Sulfuric Acid → HCID 57835419, compound

HRID 730965Notes

Reaction equation

HRID 730965 reaction equation
[CH2:1]([C:3]([C:14]1[S:18][C:17]2[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=[CH:22][C:16]=2[CH:15]=1)([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].OS(O)(=O)=O.[C:31]([O-])(O)=O.[Na+]>CO>[CH3:31][O:24][C:23]([C:20]1[CH:21]=[CH:22][C:16]2[CH:15]=[C:14]([C:3]([CH2:4][CH3:5])([C:6]3[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[CH:7]=3)[CH2:1][CH3:2])[S:18][C:17]=2[CH:19]=1)=[O:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57835416HCID 57835416, compound

Product 1

HCID 57835419HCID 57835419, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzo[b]thiophene-6-carboxylic acid (3.98 g, 11.23 mmol) in MeOH (100 mL) is treated with H2SO4 (concentrated, 1.0 mL). The mixture is stirred at 80° C. for 8 h and neutralized with aqueous NaHCO3. The MeOH is removed under vacuum and the residue is extracted with EtOAc (2×100 mL). The combined organic layer is dried over Na2SO4, concentrated and purified by silica gel column chromatography (20% EtOAc/Hex) to give the product (4.05 g, 98%).

Workup

  1. customThe MeOH is removed under vacuum
  2. extractionthe residue is extracted with EtOAc (2×100 mL)
  3. dry with materialThe combined organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (20% EtOAc/Hex)

Sources & evidence

ORD record
ord-f2ff77d2feac4ed783ea0961367bfe6f
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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