Potassium Hydroxide → HCID 59191422, compound

HRID 1023902Notes

Reaction equation

HRID 1023902 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][C:13]=2[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=O)=O)=CC=1.[OH-].[K+]>C(O)C.O>[CH2:22]([O:21][C:13]1[CH:14]=[C:15]([CH2:18][CH2:19][CH3:20])[CH:16]=[CH:17][C:12]=1[OH:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59191346HCID 59191346, compound

Product 1

HCID 59191422HCID 59191422, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(benzyloxy)-4-propylphenyl 4-methylbenzenesulfonate (0.07 mmol; 28 mg) under argon, in a mixture of ethanol (0.2 mL) and water (0.1 mL), was added KOH (0.09 mmol; 5 mg). The reaction was refluxed for 1 hr, then hydrolysed with NH4Cl sat. (3 mL), and extracted with ethyl acetate (3*5 mL). Combined organic phases were washed with saturated NaHCO3 (3 mL), dried over MgSO4, concentrated. The residue was purified by preparative TLC (cyclohexane/dichlorométhane) to yield the title compound as a clear oil (16 mg; 0.06 mmol; 86%).

Workup

  1. temperatureThe reaction was refluxed for 1 hr
  2. extractionhydrolysed with NH4Cl sat. (3 mL), and extracted with ethyl acetate (3*5 mL)
  3. washCombined organic phases were washed with saturated NaHCO3 (3 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (cyclohexane/dichlorométhane)

Sources & evidence

ORD record
ord-a7876c677d1840a5a355a6918db8646e
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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