Hydrochloric Acid → 5-(p-Heptyloxybenzyloxy)-1-methoxy-2-indaneacetic acid

HRID 982216Notes

Reaction equation

HRID 982216 reaction equation
[CH2:1]([O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH:20]([O:24][CH3:25])[CH:19]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:18]3)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[Na+].Cl>O1CCCC1.CO.O>[CH2:1]([O:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH:20]([O:24][CH3:25])[CH:19]([CH2:26][C:27]([OH:29])=[O:28])[CH2:18]3)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53634688Ethyl 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetate

Product 1

HCID 198826775-(p-Heptyloxybenzyloxy)-1-methoxy-2-indaneacetic acidYield 72.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1 ml of tetrahydrofuran and 8 ml of methanol were dissolved 220 mg of ethyl 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetate obtained in Example 4. After 1 ml of a 5% aqueous sodium hydroxide solution was added to the solution, the mixture was stirred at room temperature for 8 hours. After diluting with water, the system was rendered acidic with hydrochloric acid followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried and concentrated. The obtained crystalline residue was recrystallized from ether-pentane to obtain 150 mg of 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetic acid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained crystalline residue was recrystallized from ether-pentane

Sources & evidence

ORD record
ord-0df0b59809f54b6d9df1e610d2b9ad57
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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