Acetic Acid → HCID 20063336, compound

HRID 1084454Notes

Reaction equation

HRID 1084454 reaction equation
C([O:3][C:4]([C:6]1(C(OCC)=O)[C:16](O)([CH:17]([CH3:19])[CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7]1)=[O:5])C.C(O)(=O)C.Cl.C(=O)([O-])O.[Na+]>O>[CH:17]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7][C:6]=1[C:4]([OH:5])=[O:3])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20063323HCID 20063323, compound

Product 1

HCID 20063336HCID 20063336, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of crude 3,3-bis(ethoxycarbonyl)-4-hydroxy-4-isopropyl-3,4-dihydroisocoumarin (76 g), glacial acetic acid (500 ml) and concentrated hydrochloric acid (800 ml) was refluxed for 18 hours. The cooled mixture was added to ice/water (3500 ml) and the precipitated solid filtered off and washed with water to give an off-white solid. This was treated with a solution of sodium hydrogen carbonate (40 g) in water (400 ml) and the resultant solution was extracted with diethyl ether (150 ml). The aqueous phase was acidified to pH1 with concentrated hydrochloric acid and the white precipitate filtered off, washed with water and dried at 70° C. to give 4-isopropylisocoumarin-3-carboxylic acid (20.16 g) in the form of a white solid [Elemental analysis: C, 67.4; H, 5.2%; calculated: C, 67.2; H, 5.17%; NMR (in DMSO-d6): 1.45 (6H, d, J=8 Hz), 3.85 (1H, sept, J=8 Hz), 7.6-8.4 (4H, m)].

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationthe precipitated solid filtered off
  3. washwashed with water
  4. customto give an off-white solid
  5. extractionthe resultant solution was extracted with diethyl ether (150 ml)
  6. filtrationthe white precipitate filtered off
  7. washwashed with water
  8. customdried at 70° C.

Sources & evidence

ORD record
ord-7ecfebc3723645c8a8d71f83e2d8acdb
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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