Hydrochloric Acid → HCID 85390991, compound

HRID 1883231Notes

Reaction equation

HRID 1883231 reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[C:6]([CH3:28])[CH:7]=[CH:8][CH:9]=[C:10]([C:12]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[C:14]([CH:21]([CH3:23])[CH3:22])[C:13]=1[O:24][CH2:25][CH2:26][CH3:27])[CH3:11])C.[OH-].[Na+].Cl>CCO>[CH:21]([C:14]1[C:13]([O:24][CH2:25][CH2:26][CH3:27])=[C:12]([C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]([CH3:28])=[CH:5][C:4]([OH:29])=[O:3])[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=1)([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 85292847HCID 85292847, compound2×

Product 1

HCID 85390991HCID 85390991, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-(3,5-diisopropyl-2-propoxy-phenyl)-3-methyl-octa-2, 4,6-trienoic acid ethyl ester (Compound 15, 2.45 g, 6.16 mmol) in EtOH (50 mL) was treated with 1M NaOH (25 mL, 25 mmol) and was heated to 80° C. for 4 h. The mixture was cooled to room temperature, acidified with 1M HCl, and was extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by recrystallization from CH3CN to yield the title compound as a white solid (1.87 g, 82%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionwas extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by recrystallization from CH3CN

Sources & evidence

ORD record
ord-36bf94e9211144f99495251e0a81b2b4
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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