4-Chlorophenol → 1-Chloro-4-(2,2-diethoxyethoxy)benzene

HRID 1403339Notes

Reaction equation

HRID 1403339 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H][H].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17]Br)[CH3:14]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH:16]([O:19][CH2:20][CH3:21])[O:15][CH2:13][CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 5685551-Chloro-4-(2,2-diethoxyethoxy)benzeneYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of sodium hydride (11.24 g, 281 mmol) in anhydrous N,N-dimethylformamide (500 mL) was added 4-chlorophenol (30 g, 234 mmol) at 0° C. After hydrogen evolution had ceased, bromo-acetaldehyde diethyl acetal (55 g, 281 mmol) was added. The reaction was heated at 120° C. overnight. The mixture was poured into ice-water, extracted with ethyl acetate (3×150 ml), washed with 1N sodium hydroxide (3×100 ml), and brine (3×100 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. The residue was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 1-chloro-4-(2,2-diethoxyethoxy)benzene as oil (45 g, 75%).

Workup

  1. extractionextracted with ethyl acetate (3×150 ml)
  2. washwashed with 1N sodium hydroxide (3×100 ml), and brine (3×100 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum
  6. customThe residue was purified by a silica gel column with 1% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b1aadb4d5f0a47db9674efc904e04631
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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