Methanol → HCID 15229923, compound

HRID 1721653Notes

Reaction equation

HRID 1721653 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]([O: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].CCCCCC>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]([O: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

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 14798Sodium Hydroxide2×HCID 15229921HCID 15229921, compound

Product 1

HCID 15229923HCID 15229923, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g (11.7 mmol) of methyl (E)-6-(4-cyano-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate and 1.86 g (46.5 mmol) of sodium hydroxide in 100 ml of 3:2 water:methanol was heated at reflux for 2 hours. The resulting homogenous solution was distilled until 30 ml of distillate was recovered. An additional 0.6 g (15 mmol) of sodium hydroxide was added to the reaction solution and it was refluxed for 2 days. Upon cooling the solution was partitioned between 1N aqueous HCl and ethyl acetate. The organic phase was washed twice with water, once with brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a solid. This solid was stirred with hexane and then filtered off to give 3.88 g (11.1 mmol) of (E)-6-(4-carboxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid as a white solid, mp 172°-174° C.

Workup

  1. temperatureat reflux for 2 hours
  2. distillationThe resulting homogenous solution was distilled until 30 ml of distillate
  3. customwas recovered
  4. temperaturewas refluxed for 2 days
  5. temperatureUpon cooling the solution
  6. customwas partitioned between 1N aqueous HCl and ethyl acetate
  7. washThe organic phase was washed twice with water, once with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customto give a solid
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-e6558a446cf4497983e27122f72f3136
Source dataset
uspto-grants-1996_04
Patent number
US05512568

Reaction notes

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