1,10-Dibromodecane → HCID 19874510, compound

HRID 465456Notes

Reaction equation

HRID 465456 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Na].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CO>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Br:13])=[CH:7][CH:6]=1)[C:9]([CH3:10])=[O:11]

Participants

5

Reactant 3

HCID 2214831,10-DibromodecaneHCID 5360545SodiumHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 19874510HCID 19874510, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 4-hydroxyphenyl propan-2-one, ethylene ketal (5.26 g) in methanol at room temperature, was treated with sodium (0.66 g) and allowed to stir for 10 minutes. The resulting solution was then added dropwise over 15 minutes to a solution of 1,10-dibromodecane (9.0 g) in methanol under reflux and the reaction mixture heated for 3 h. The mixture was allowed to cool and the solvent was removed in vacuo. The residue was partitioned between diethylether and water, the organic layer separated, dried (magnesium sulphate), and the solvent removed in vacuo to give an oil which was chromatographed on silica. Elution with chloroform gave 10-(4-acetonylphenoxy)decyl bromide, ethylene ketal (3.0 g) as an oil.

Workup

  1. temperatureunder reflux
  2. temperaturethe reaction mixture heated for 3 h
  3. temperatureto cool
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned between diethylether and water
  6. customthe organic layer separated
  7. dry with materialdried (magnesium sulphate)
  8. customthe solvent removed in vacuo
  9. customto give an oil which
  10. customwas chromatographed on silica
  11. washElution with chloroform

Sources & evidence

ORD record
ord-fcfddcfa47c7487293673cf9c020c254
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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