Sodium Hydroxide → Diethyl 2-(3-butenyloxy)terephthalate

HRID 128842Notes

Reaction equation

HRID 128842 reaction equation
[OH:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[OH-].[Na+].Br[CH2:21][CH2:22][CH:23]=[CH2:24]>CN(C)C=O>[CH2:24]([O:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:23][CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21241Homoallyl bromideHCID 22401614Diethyl 2-hydroxybenzene-1,4-dicarboxylate

Product 1

HCID 22401611Diethyl 2-(3-butenyloxy)terephthalateYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.55 g of this diethyl hydroxyterephthalate was dissolved in 100 mL dimethylformamide and combined with 640 mg crushed sodium hydroxide. 4.03 g 4-bromo-1-butene dissolved in 20 mL dimethylformamide was added dropwise in while cooling on an ice bath. After stirring the reaction for 16 hours, purification by the usual methods gave 1.8 g diethyl 2-(3-butenyloxy)terephthalate.

Workup

  1. additionwas added dropwise in
  2. temperaturewhile cooling on an ice bath
  3. customthe reaction for 16 hours
  4. custompurification by the usual methods

Sources & evidence

ORD record
ord-a83e70ef3b574d0c8405ef76c3c07686
Source dataset
uspto-grants-1995_11
Patent number
US05464922

Reaction notes

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