Hydrochloric Acid → HCID 85074544, compound

HRID 1883227Notes

Reaction equation

HRID 1883227 reaction equation
C([O:3][C:4](=[O:30])[CH:5]=[C:6]([CH3:29])[CH:7]=[CH:8][CH:9]=[C:10]([C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:16]=[C:15]([CH:22]([CH3:24])[CH3:23])[C:14]=1[O:25][CH2:26][CH2:27][CH3:28])[CH2:11][CH3:12])C.[OH-].[Na+].Cl>CCO>[CH:22]([C:15]1[C:14]([O:25][CH2:26][CH2:27][CH3:28])=[C:13]([C:10]([CH2:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]([CH3:29])=[CH:5][C:4]([OH:30])=[O:3])[CH:18]=[C:17]([CH:19]([CH3:20])[CH3:21])[CH:16]=1)([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72647293HCID 72647293, compound2×

Product 1

HCID 85074544HCID 85074544, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-(3,5-diisopropyl-2-propoxy-phenyl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Compound 7, 11.4 g, 27.7 mmol) in EtOH (220 mL) was treated with 1M NaOH (111 mL, 111 mmol) and was heated to 80 ° C. for 3 h. The mixture was cooled to room temperature, acidified with 1M HCl (115 mL), 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 an off-white solid (7.56 g, 71%).

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-f7751f3bb26a4aa0afc4d19c945f35d7
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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