5-(Benzyloxy)pentan-1-ol → 5-(Benzyloxy)pentanoic acid

HRID 1367664Notes

Reaction equation

HRID 1367664 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:3])=[O:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2211945-(Benzyloxy)pentan-1-olHCID 131709961Jones' reagent2×

Product 1

HCID 104205755-(Benzyloxy)pentanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Jones reagent was added dropwise to an ice cooled solution of 5-benzyloxy-pentan-1-ol 28 (5 g, 25.74 mmol) in acetone (170 ml). Addition of the Jones reagent was stopped when the acetone solution acquired a persistent yellow color with the concurrent formation of green chlomium salts. The mixture was filtered and concentrated in vacuo to give an oily crude product that was purified by a flash chromatography (EtOAc/hexanes, 1:3) to give compound 29 (4.98 g, 93%) as a colorless oil: TLC Rf=0.68 (silica gel, 50% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 7.35-7.31 (m, 5H), 4.502 (s, 2H), 3.51-3.47 (t, 3J=6 Hz, 2H), 2.41-2.36 (t, 3J=6.8 Hz, 2H), 1.79-1.64 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 179.713, 138.651, 128.609, 127.870, 127.795, 73.158, 69.968, 33.915, 29.243, 21.749; HRMS calcd for C12H16O3+Na+ 231.0997; found 231.0992 [M+Na+].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give an oily crude product that
  4. customwas purified by a flash chromatography (EtOAc/hexanes, 1:3)

Sources & evidence

ORD record
ord-74ab7ccd3e034077891ac9eb34935138
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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