Hydrochloric Acid → HCID 11406375, compound

HRID 2180559Notes

Reaction equation

HRID 2180559 reaction equation
[CH2:1]([O:3][C:4]1[C:5](/[C:17](/[CH2:29][CH3:30])=[CH:18]\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[C:23]([O:25]CC)=[O:24])=[CH:6][C:7]2[C:8]([CH3:16])=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH2:1]([O:3][C:4]1[C:5](/[C:17](/[CH2:29][CH3:30])=[CH:18]\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[C:23]([OH:25])=[O:24])=[CH:6][C:7]2[C:8]([CH3:16])=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 87972449HCID 87972449, compound

Product 1

HCID 11406375HCID 11406375, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 7-(3-ethoxy-5,5,8-trimethyl-5,6-dihydronaphthalen-2-yl)-3-methyl-nona-2E,4E,6Z-trienoate (Compound A-13, 0.82 g, 2.01 mmol) in ethanol (5 mL) and THF (5 mL) was treated with 2M NaOH (5 mL, 10 mmol) and then stirred at 50° C. for 5 h. The mixture was cooled to room temperature, acidified with 10% HCl, and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by recrystallization from acetonitrile to yield the title compound as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  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 acetonitrile

Sources & evidence

ORD record
ord-a4724f1f7fb94397b60a67c29ef1c51d
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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