Potassium Hydroxide → Acyclic retinoid

HRID 1611061Notes

Reaction equation

HRID 1611061 reaction equation
[OH-].[K+].[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5]\[C:6]([O:8]CC)=[O:7]>CC(O)C>[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:26])/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5]\[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11984134Ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoate

Product 1

HCID 6437836Acyclic retinoidYield 51%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Potassium hydroxide (3.0 g) was dissolved in 20 ml of 2-propanol at 100° C. The solution was added with 2-propanol (10 ml) solution of ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoate obtained in Example 1, and stirred at the same temperature for 5 minutes. The reaction mixture was added to ice-water and washed with n-hexane. The solution was neutralized with 10% hydrochloric acid and extracted with n-hexane. The resulting organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from methanol to obtain 3.5 g of the title compound (yield 51%) as a yellow crystal.

Workup

  1. washwashed with n-hexane
  2. extractionextracted with n-hexane
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e9886ed1a69f4156afd31277a8ccb8cb
Source dataset
uspto-grants-2006_01
Patent number
US06984742B2

Reaction notes

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