Hydrochloric Acid → HCID 15106532, compound

HRID 847299Notes

Reaction equation

HRID 847299 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:27][C:28]([O:30]CC)=[O:29].[OH-].[Na+].Cl>CO>[OH:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:18]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:27][C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53924721HCID 53924721, compound

Product 1

HCID 15106532HCID 15106532, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 380 mg of ethyl 1-hydroxy-4-(p-heptyloxybenzyloxy)-2-indaneacetate obtained in Example 100 and, 2.5 ml of a 5% sodium hydroxide solution was added thereto followed by stirring at room temperature for 8 hours. The system was rendered acidic with 20% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed subsequently with water and then a saturated saline aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystalline residue was recrystallized from ethyl acetate-hexane to obtain 230 mg of 1-hydroxy-4-(p-heptyloxybenzyloxy)-2-indaneacetic acid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed subsequently with water
  4. dry with materiala saturated saline aqueous solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crystalline residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-05fc5712c8b14adfacc74931e412d954
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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