Water → HCID 6430171, compound

HRID 2055077Notes

Reaction equation

HRID 2055077 reaction equation
[CH2:1]([CH:14]1OCC[O:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[CH:14](=[O:15])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 17959806HCID 17959806, compound

Product 1

HCID 6430171HCID 6430171, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.89 g 2-[(E)tridec-7-enyl]-1,3-dioxolane (9), 30 mg p-toluenesulphonic acid and 25 ml of water were boiled in 75 ml methanol for 72 h under reflux under blanketing gas (86% conversion). The reaction mixture was extracted twice with 200 ml diethyl ether, washed with 30 ml sodium bicarbonate solution and dried over sodium sulphate and the solvent was distilled off under vacuum. Flash chromatography on silica gel gave (E)-8-tetradecenal (10) (E/Z ratio according to GC>97/3).

Workup

  1. temperatureunder reflux under blanketing gas (86% conversion)
  2. extractionThe reaction mixture was extracted twice with 200 ml diethyl ether
  3. washwashed with 30 ml sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-d4606d6a9db54e588d9294b23d1060bc
Source dataset
uspto-grants-2008_02
Patent number
US07332468B2

Reaction notes

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