tert-Butanol → 56219-51-3

HRID 1788816Notes

Reaction equation

HRID 1788816 reaction equation
[OH-].[K+].C(O)(C)(C)C.[CH2:8]1[O:16][C:15]2[CH:14]=[CH:13][C:12]([OH:17])=[CH:11][C:10]=2[O:9]1.[Br:18][CH2:19][CH2:20][CH2:21]Br>O>[Br:18][CH2:19][CH2:20][CH2:21][O:17][C:12]1[CH:13]=[CH:14][C:15]2[O:16][CH2:8][O:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 68289Sesamol

Product 1

HCID 1091221656219-51-3Yield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution prepared by dissolving 7.3 g of potassium hydroxide in 7 ml of water and then adding 120 ml of t-butanol are added 15 g of 3,4-methylenedioxyphenol and 88 g of 1,3-dibromopropane and the mixture is stirred for 3 hours under heating at reflux. After completion of the reaction, the solvent is distilled off and benzene is added and washed with water. The benzene layer is dried over anhydrous sodium sulfate and the solvent is distilled off. The residue is subjected to vacuum distillation to give 23 g of 5-(3-bromopropoxy)-1,3-benzodioxole boiling at 120° C./1 mmHg.

Workup

  1. customTo a solution prepared
  2. temperatureunder heating
  3. temperatureat reflux
  4. customAfter completion of the reaction
  5. distillationthe solvent is distilled off
  6. additionbenzene is added
  7. washwashed with water
  8. dry with materialThe benzene layer is dried over anhydrous sodium sulfate
  9. distillationthe solvent is distilled off
  10. distillationThe residue is subjected to vacuum distillation

Sources & evidence

ORD record
ord-db112047c19e43b3a1f1f3e0cc3d9b0d
Source dataset
uspto-grants-1987_08
Patent number
US04684739

Reaction notes

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