Cycloheptene → 2-[(1-Cyclohepten-3-yl)thio]acetaldehyde

HRID 46738

Reaction equation

HRID 46738 reaction equation
[CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH2:8].C1(C)C=C[C:12]([S:15](O)(=O)=O)=[CH:11]C=1>CC(C)=O.O>[CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([S:15][CH2:12][CH:11]=[O:8])[CH:2]=1

Participants

4

Reactant 2

HCID 12363CyclohepteneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 126209612-[(1-Cyclohepten-3-yl)thio]acetaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 108.13 g (0.443 mole) of 3-[2,2-diethoxyethyl)thio]-1-cycloheptene in 1000 ml of acetone/water, 9:1 was treated with 1.1 g of p-toluenesulfonic acid hydrate and heated under reflux for 1.0 hour, cooled, and concentrated. The residue was partitioned between ether/10% sodium bicarbonate. The aqueous phase was further extracted with ether. The organic extracts were pooled, dried over magnesium sulfate, and evaporated to afford 75.30 g (0.443 mole, 100%) of 2-[(1-cyclohepten-3-yl)thio]acetaldehyde as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.0 hour
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between ether/10% sodium bicarbonate
  6. extractionThe aqueous phase was further extracted with ether
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-d2e4355203d449d08f1cb4c0210246dc
Source dataset
uspto-grants-1979_11
Patent number
US04175086

Linked notes

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