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

HRID 369676Notes

Reaction equation

HRID 369676 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 to the reaction mixture, which was stirred 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 magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 21.6 g of 4-(2,2-diethoxyethoxy)butanol (yield, 41%), nD23.2 1.4314.

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. stirringwas stirred at 60° C. for 8 hours
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

Sources & evidence

ORD record
ord-d5fdb1f5492b44dc824cda1ab4cdee9d
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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