Hydrochloric Acid → HCID 15171579, compound

HRID 1493727Notes

Reaction equation

HRID 1493727 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=2[CH2:37][CH2:38][CH3:39])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=2[CH2:37][CH2:38][CH3:39])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15171575HCID 15171575, compound

Product 1

HCID 15171579HCID 15171579, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]butanoate (example 1, 1.7 g) in ethanol (5 ml) was added a solution of sodium hydroxide (0.38 g) in water (5 ml). The mixture was heated on water-bath for 10 minutes, poured into ice water, made acidic with concentrated hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-methanol (10:1). Recrystallization from benzene-n-hexane afforded the title compound (0.99 g, 61.4%) as colorless crystals, mp 50°-53° C.

Workup

  1. temperatureThe mixture was heated on water-bath for 10 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane-methanol (10:1)
  8. customRecrystallization from benzene-n-hexane

Sources & evidence

ORD record
ord-ab58ed33ed6e4a1d9ed4b02d134b50d7
Source dataset
uspto-grants-1991_06
Patent number
US05023364

Reaction notes

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