Sodium Sulfite → 3,3,4-Trimethylpentanal

HRID 1806851Notes

Reaction equation

HRID 1806851 reaction equation
[CH3:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[CH2:3][CH2:4][OH:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[CH3:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[CH2:3][CH:4]=[O:5]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 124253343,3,4-Trimethylpentan-1-ol

Product 1

HCID 124253353,3,4-TrimethylpentanalYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step C To a solution of 3,3,4-trimethyl-pentan-1-ol (5.4 g, 41 mmol) in dichloromethane (100 mL) was added Dess-Martin periodinane (22 g 52 mmol) The reaction mixture was stirred at room temperature for 3 h. Aqueous Na2SO3 solution was added to quench the reaction. The organic layers were separated, washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:30) to give 3,3,4-trimethyl-pentanal as a colorless oil (Yield: 1.1 g, 21%).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layers were separated
  4. washwashed with saturated NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1:30)

Sources & evidence

ORD record
ord-04793b282781441ba373943a0ab4286c
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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