2-Bromoethanol → 4-Methoxybenzyl 4-(2-hydroxyethoxy)benzoate

HRID 489054Notes

Reaction equation

HRID 489054 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][OH:29]>CN(C)C=O>[OH:29][CH2:28][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:7])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 12119266Benzoic acid, 4-hydroxy-, (4-methoxyphenyl)methyl ester

Product 1

HCID 220358874-Methoxybenzyl 4-(2-hydroxyethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4methoxybenzyl 4-hydroxybenzoate (7.0 g, 27 mmole) in dry N,N-dimethylformamide (50 ml) was added potassium carbonate (4.15 g, 30 mmole) and 2-bromoethanol. The mixture was stirred 48 hours at 80° C., evaporated under reduced pressure and ethyl acetate and water were added. The organic phase was washed five times with water and dried with sodium sulfate. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromatography with hexane/ethyl acetate.

Workup

  1. customevaporated under reduced pressure and ethyl acetate and water
  2. additionwere added
  3. washThe organic phase was washed five times with water
  4. dry with materialdried with sodium sulfate
  5. customThe solution was evaporated under reduced pressure
  6. customthe product was isolated by silica gel column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-56de8da4c96c4ccfa0e5cd1e23012a6e
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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