Water → HCID 18984240, compound

HRID 1439831Notes

Reaction equation

HRID 1439831 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:11][OH:12])[CH2:9][OH:10].O.[C:14]1(C)[CH:19]=CC(S(O)(=O)=O)=C[CH:15]=1.O>C1C=CC=CC=1.CC(C)=O>[CH3:15][C:14]1([CH3:19])[O:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH2:11][O:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 18984239HCID 18984239, compound

Product 1

HCID 18984240HCID 18984240, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

24.2 g of crude 2-(6-bromohexyl)-1,3-propanediol was dissolved in a mixture of 200 mL of benzene, 30 mL acetone, and 0.4 g toluene-4-sulfonic acid monohydrate (Fluka, puriss.) in a 1 L 1-necked round flask. While magnetically stirring and refluxing 1.4 mL of water was separated and collected in a Dean-Stark trap during 22 h. The solvents were removed by rotary evaporation under reduced pressure and the residue vacuum distilled to recover 14.65 g of 2,2-dimethyl-5-(6-bromohexyl)-m-dioxane with b.p. 96°-97° C./0.06 mbar.

Workup

  1. customwas separated
  2. customcollected in a Dean-Stark trap during 22 h
  3. customThe solvents were removed by rotary evaporation under reduced pressure
  4. distillationthe residue vacuum distilled
  5. customto recover 14.65 g of 2,2-dimethyl-5-(6-bromohexyl)-m-dioxane with b.p. 96°-97° C./0.06 mbar

Sources & evidence

ORD record
ord-e7eb85e4067c47d599db66783270dcb8
Source dataset
uspto-grants-1996_03
Patent number
US05496670

Reaction notes

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