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

HRID 1018808Notes

Reaction equation

HRID 1018808 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 heated to reflux. 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. The residue is purified by chromatography on a column of silica gel, eluting with cyclohexane; yield=80%.

Workup

  1. temperaturethe mixture is heated to reflux
  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. customThe residue is purified by chromatography on a column of silica gel
  9. washeluting with cyclohexane

Sources & evidence

ORD record
ord-e2f6148912ff4a3ab4d78ad70ad4bb08
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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