Isopropanol → 77092-47-8

HRID 1897609Notes

Reaction equation

HRID 1897609 reaction equation
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].Br[CH2:8][CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C(Cl)Cl>[CH2:11]([O:10][CH:9]([O:13][CH2:14][CH3:15])[CH2:8][O:6][CH:3]([CH3:5])[CH3:4])[CH3:12]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 1260015077092-47-8

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaH (3.35 g, 84 mmol) was added to isopropanol (5.38 mL, 69.9 mmol) at 0° C. The reaction mixture was stirred at room temperature for 30 min followed by the addition of 2-bromo-1,1-diethoxyethane (7.89 mL, 52.4 mmol). The tube was sealed, heated to 120° C. and stirred overnight. The sealed tube was cooled to room temperature and the contents were dissolved in DCM and washed with water twice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give 2-(2,2-diethoxy-ethoxy)-propane, which was hydrolyzed according to the method described in example 29 to give crude isopropoxy-acetaldehyde.

Workup

  1. customThe tube was sealed
  2. temperatureheated to 120° C.
  3. stirringstirred overnight
  4. temperatureThe sealed tube was cooled to room temperature
  5. washwashed with water twice
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4b473e1800146bcbd7c953911ff36d5
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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