2-Bromoethanol → 2-(3,4-Dimethoxyphenoxy)ethanol

HRID 496033Notes

Reaction equation

HRID 496033 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([OH:17])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].Br[CH2:19][CH2:20][OH:21]>CN(C=O)C.CCOC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[O:17][CH2:19][CH2:20][OH:21]

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 162513,4-Dimethoxyphenol

Product 1

HCID 122988832-(3,4-Dimethoxyphenoxy)ethanolYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

K2CO3 (1.07 g, 7.78 mmol) was added to a solution of 3,4,dimethoxyphenol (1.0 g, 6.48 mmol) in dry DMF (15 ml). 2-Bromoethanol (0.81 g, 6.48 mmol) was added, and the mixture was heated overnight at 120° C. The mixture was cooled, taken up in EtOAc, extracted with water (20 ml), saturated NaCl (4×20 ml), dried over MgSO4, and evaporated under reduced pressure. The product was purified by column chromatography on silica (Hexane:EtOAc 3:1) to give the desired product in 60% yield. B. Synthesis of 4-(2-bromo-ethoxy)-1,2-dimethoxy benzene

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with water (20 ml), saturated NaCl (4×20 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe product was purified by column chromatography on silica (Hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-ea5b61dfd50746b4b6f1e99a6c33b1e7
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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