Bis(acetoxy)iodobenzene → 3-Hydroxy-2,2-dimethyl-5-phenylpentanal

HRID 516655Notes

Reaction equation

HRID 516655 reaction equation
C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.[CH3:16][C:17]([CH3:30])([CH:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][OH:19].O.C(=O)(O)[O-].[Na+]>ClCCl>[OH:29][CH:20]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]([CH3:16])([CH3:30])[CH:18]=[O:19]

Participants

5

Reactant 3

HCID 21865429Bis(acetoxy)iodobenzeneHCID 855939482,2-Dimethyl-5-phenyl-1,3-pentanediolHCID 86585896Sodium bicarbonate water

Product 1

HCID 157865963-Hydroxy-2,2-dimethyl-5-phenylpentanalYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMN-AZADO (2.00 mg, 0.012 mmol) and diacetoxyiodobenzene (117 mg, 0.362 mmol) were added to a dichloromethane solution (0.24 ml) of 2,2-dimethyl-5-phenylpentane-1,3-diol (50.2 mg, 0.241 mmol), and the mixture was stirred at room temperature for 15 min. This was followed by addition of saturated sodium bicarbonate water (1 ml) and a sodium thiosulfate solution (1 ml), and extraction with diethyl ether. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 3-hydroxy-2,2-dimethyl-5-phenylpentanal (49.2 mg, 92%).

Workup

  1. extractiona sodium thiosulfate solution (1 ml), and extraction with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b088dd1a3b264c0e82bd6badb58f889f
Source dataset
uspto-grants-2015_08
Patent number
US09114390B2

Reaction notes

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