Water → Benzyl 3,6,9,12-tetraoxatridecanoate

HRID 440453Notes

Reaction equation

HRID 440453 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].Br[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH2:13][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8178Triethylene glycol monomethyl etherHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 54493198Benzyl 3,6,9,12-tetraoxatridecanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethyleneglycol monomethyl ether (10 mmol) and benzyl bromoacetate (11 mmol) are added to a suspension of anhydrous K2CO3 (15 mmol) in 50 ml anhydrous DMF. The suspension is stirred at room temperature overnight. Water is added and the emulsion is extracted with ethyl acetate (3×200 ml), washed with water, brine, and dried with MgSO4. The solvent is evaporated and the residual oil purified by flash chromatography to give the title compound.

Workup

  1. extractionthe emulsion is extracted with ethyl acetate (3×200 ml)
  2. washwashed with water, brine
  3. dry with materialdried with MgSO4
  4. customThe solvent is evaporated
  5. customthe residual oil purified by flash chromatography

Sources & evidence

ORD record
ord-a7f6c9926bf9449fb3b726f30e32a640
Source dataset
uspto-grants-1996_05
Patent number
US05519134

Reaction notes

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