Benzyl Bromide → Benzyl (2-methoxyethoxy)acetate

HRID 987298Notes

Reaction equation

HRID 987298 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=[O:8].[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([O:9][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 27642(2-Methoxyethoxy)acetic acid

Product 1

HCID 22988705Benzyl (2-methoxyethoxy)acetateYield 104%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2-Methoxyethoxy)acetic acid (10 g; 75 mmole) and tetrabutylammonium bromide (25.3 g; 75 mmole) were dissolved in sodium hydoxide solution (2 M; 75 ml; 75 mmole). Benzyl bromide (15.3 g; 89 mmole) dissolved in dichloromethane (150 ml) was added. The reaction mixture was refluxed 4 hours. After separation the organic phase was dried with magnesium sulfate and evaporated. Chromatography using dichloromethane as eluant gave 17.5 g (94%) of benzyl 2-(2-methoxyethoxy)acetate.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed 4 hours
  3. customAfter separation the organic phase
  4. dry with materialwas dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2431762079e84024bffe2b11d9616831
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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