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

HRID 861661Notes

Reaction equation

HRID 861661 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-b5b724188b8849bdb24b6f9866599d9d
Source dataset
uspto-grants-1998_02
Patent number
US05714606

Reaction notes

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