Dichloromethane → 3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenylethyne

HRID 1071923Notes

Reaction equation

HRID 1071923 reaction equation
[OH-].[Na+].Cl[C:4]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[C:10]([Cl:24])[CH:9]=1)=[CH:5]C=O.ClCCl>O.O1CCOCC1>[Cl:24][C:10]1[CH:9]=[C:8]([C:4]#[CH:5])[CH:13]=[CH:12][C:11]=1[CH:14]1[CH2:19][C:18]([CH3:20])([CH3:21])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 572145173-Chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal

Product 1

HCID 113693783-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenylethyneYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

5.3 g of sodium hydroxide are dissolved in 150 ml of water under an inert atmosphere and with vigorous stirring. 80 ml of 1,4-dioxane are added and the mixture is refluxed. 15 g of 3-chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal (compound IV.1) dissolved in 130 ml of 1,4-dioxane are added rapidly, and the reaction mixture is maintained at reflux for 1 hour. After cooling to room temperature, the reaction mixture is poured into a large volume of dichloromethane. The phases are separated after settling has taken place, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. Purification is carried out by chromatography on a column of silica gel, eluting with cyclohexane; yield: 80%.

Workup

  1. temperaturethe mixture is refluxed
  2. additionare added rapidly
  3. temperaturethe reaction mixture is maintained
  4. temperatureat reflux for 1 hour
  5. customThe phases are separated after settling
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. customthe solvents are evaporated off under reduced pressure
  8. customPurification
  9. washeluting with cyclohexane

Sources & evidence

ORD record
ord-61d3efaff8624ace83f23cb7d8921960
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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