Hydrochloric Acid → HCID 23021543, compound

HRID 501772Notes

Reaction equation

HRID 501772 reaction equation
[CH:1]1([O:6][C:7]2[CH:40]=[CH:39][C:10]([C:11]([C:13]3[CH:32]=[CH:31][C:16]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=4)=[C:15]([CH2:33][CH2:34][C:35]([O:37]C)=[O:36])[CH:14]=3)=[O:12])=[C:9]([OH:41])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.Cl.C(OCC)(=O)C>CO.O1CCCC1.[OH-].[Na+]>[C:35]([CH2:34][CH2:33][C:15]1[CH:14]=[C:13]([C:11](=[O:12])[C:10]2[CH:39]=[CH:40][C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:8][C:9]=2[OH:41])[CH:32]=[CH:31][C:16]=1[O:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=1)([OH:37])=[O:36]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 68458090HCID 68458090, compound

Product 1

HCID 23021543HCID 23021543, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.98 g of methyl 4-{[4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-(3-methoxy-3-oxopropyl)phenoxy]methyl}-2-methoxybenzoate was dissolved in a mixed solvent of 10 mL of methanol and 10 mL of tetrahydrofuran, to which 2 mL of a 20% aqueous solution of sodium hydroxide was added at room temperature, and then this mixture was stirred for one hour at the same temperature. The reaction mixture to which water was added was adjusted to pH 2 with 6M hydrochloric acid, followed by the addition of ethyl acetate thereto, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, this washed phase was dried over anhydrous magnesium sulfate and the solvent was distilled out under reduced pressure. The resultant residue was recrystallized from ethanol to yield 0.42 g of 4-({2-(2-carboxyethyl)-4-[4-(cyclopentyloxy)-2-hydroxybenzoyl]phenoxy}methyl)-2-methoxybenzoic acid as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, this washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ef7cd289bb5740f29c0cdcbf6aa85454
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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