Water → Ethyl 2-(4-bromobutoxy)acetate

HRID 1288340Notes

Reaction equation

HRID 1288340 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8][OH:9])=[O:7].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.O>COCCOC.CCOCC>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][O:9][CH2:8][C:6]([O:5][CH2:4][CH3:3])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 12184Ethyl GlycolateHCID 24758Sodium hydride

Product 1

HCID 20436843Ethyl 2-(4-bromobutoxy)acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (9.0 g., 0.375 mole) is suspended in 1,2-dimethoxyethane. The mixture is stirred and cooled in an ice bath while ethyl glycollate (39.0 g., 0.375 mole) is added dropwise during one hour. 1,4-Dibromobutane (108 g., 0.5 mole) is added all at once to the resulting thick suspension. The mixture is warmed gently to initiate a strongly exothermic reaction; then the mixture is heated 3 hours on the steam bath. The mixture is poured into cold water. The heavy oil layer is taken up in ether, washed with three portions of water, and dried over sodium sulfate.

Workup

  1. additionis added dropwise during one hour
  2. temperatureThe mixture is warmed gently
  3. customa strongly exothermic reaction
  4. temperaturethen the mixture is heated 3 hours on the steam bath
  5. washwashed with three portions of water
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e0cc1c8343694b3384a27df23242cf05
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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