1,4-Butanediol → 4-(2,2-Diethoxyethoxy)butanol

HRID 1280238Notes

Reaction equation

HRID 1280238 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13]Br)[CH3:10]>CN(C)C=O>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[CH3:10]

Participants

5

Reactant 3

HCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 184301114-(2,2-Diethoxyethoxy)butanolYield 41.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 56.3 g of 1,4-butanediol and 400 ml of N,N-dimethylformamide was slowly added 11.0 g of 60% sodium hydride (in oil) with stirring under ice cooling. After stirring at room temperature for 12 hours, 49.3 g of bromoacetaldehyde diethylacetal was added dropwise, and the stirring was further continued at 60° C. for 8 hours. The reaction mixture was poured into ice water, and extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 21.6 g (yield, 41%) of 4-(2,2-diethoxyethoxy)butanol.

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-80df7fbf7d9d41468ba791b5fbc1fd38
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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