Methanol → HCID 70189712, compound

HRID 742357Notes

Reaction equation

HRID 742357 reaction equation
[C:1]([C:3]1[C:11]([CH2:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[C:10]([CH2:22][CH3:23])[C:9]([CH3:24])=[C:8]2[C:4]=1[C:5](=[O:25])[O:6][CH2:7]2)#N.[OH-:26].[Na+].C[OH:29]>O>[C:1]([C:3]1[C:11]([CH2:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[C:10]([CH2:22][CH3:23])[C:9]([CH3:24])=[C:8]2[C:4]=1[C:5](=[O:25])[O:6][CH2:7]2)([OH:29])=[O:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 86749561HCID 86749561, compound

Product 1

HCID 70189712HCID 70189712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g of methyl (E)-6-(4-cyano-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate and 1.86 g of sodium hydroxide in 100 ml of 3:2 water:methanol is heated at reflux for 2 hours. The resulting homogeneous solution is distilled until 30 ml of distillate is recovered. An additional 0.6 g (15 mmol) of sodium hydroxide is added to the reaction solution and it is refluxed for 2 days. Upon cooling the solution is partitioned between 1N aqueous HCl and ethyl acetate. The organic phase is washed twice with water, once with brine, and then dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give (E)-6-(4-carboxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid.

Workup

  1. temperatureat reflux for 2 hours
  2. distillationThe resulting homogeneous solution is distilled until 30 ml of distillate
  3. customis recovered
  4. temperatureis refluxed for 2 days
  5. temperatureUpon cooling the solution
  6. customis partitioned between 1N aqueous HCl and ethyl acetate
  7. washThe organic phase is washed twice with water, once with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-82514196762943369dc3e015b4cb9028
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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