p-Toluenesulfonic acid → HCID 86749562, compound

HRID 260115Notes

Reaction equation

HRID 260115 reaction equation
[C:1]([C:4]1[C:12]([CH2:13]/[CH:14]=[C:15](\[CH3:21])/[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:11]([CH2:22][CH3:23])[C:10]([CH3:24])=[C:9]2[C:5]=1[C:6](=[O:25])[O:7][CH2:8]2)([OH:3])=[O:2].[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:4]1[C:12]([CH2:13]/[CH:14]=[C:15](\[CH3:21])/[CH2:16][CH2:17][C:18]([O:20][CH3:26])=[O:19])=[C:11]([CH2:22][CH3:23])[C:10]([CH3:24])=[C:9]2[C:5]=1[C:6](=[O:25])[O:7][CH2:8]2)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70189712HCID 70189712, compound

Product 1

HCID 86749562HCID 86749562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.88 g of (E)-6-(4-carboxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid and 0.2 g of p-toluenesulfonic acid in methanol (60 ml) is stirred at room temperature for 8 hours. The solvent is evaporated under reduced pressure. The residue is dissolved in ethyl acetate, and this solution washed twice with water, once with brine, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give methyl (E)-6-(4-carboxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washthis solution washed twice with water, once with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2bff524ccc764b74b7a9354838133862
Source dataset
uspto-grants-1996_06
Patent number
US05525602

Reaction notes

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