(R)-3-Benzyloxy-1-tetradecanol → (R)-3-(Benzyloxy)tetradecanoic acid

HRID 233473Notes

Reaction equation

HRID 233473 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:21][C@H:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:23][CH2:24][OH:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[CH2:14]([O:21][C@H:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:23][C:24]([OH:3])=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11723551(R)-3-Benzyloxy-1-tetradecanolHCID 131709961Jones' reagent

Product 1

HCID 11110428(R)-3-(Benzyloxy)tetradecanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent was added in portions to a mixture of alcohol 46 (3.23 g, 10.1 mmol) in acetone (50 mL) at 0° C. until the alcohol was consumed. The mixture was partitioned between 0.1M HCl (100 mL) and ethyl acetate (400 mL), and the organic phases were washed with brine (100 mL), dried, and concentrated in vacuo. The product was purified by flash chromatography to give compound 47 as an oil (Rf 0.38, silica, 25% ethyl acetate in hexane, 2.09 g, 62%).

Workup

  1. customwas consumed
  2. customThe mixture was partitioned between 0.1M HCl (100 mL) and ethyl acetate (400 mL)
  3. washthe organic phases were washed with brine (100 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-566837bebd524a1d9d5ee6127012a37a
Source dataset
uspto-grants-1997_01
Patent number
US05593969

Reaction notes

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