Hydrochloric Acid → HCID 59408345, compound

HRID 2389212Notes

Reaction equation

HRID 2389212 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Cl-].[CH3:8][O:9]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:30]([C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:44][CH2:43][CH:42]([CH:45]3[CH2:50]CC(=O)C[CH2:46]3)[CH2:41][CH2:40]2)=[CH:35][CH:34]=1)[CH2:31][CH3:32].Cl>C1COCC1.O>[CH3:8][O:9][CH:1]=[C:2]1[CH2:5][CH2:50][CH:45]([CH:42]2[CH2:41][CH2:40][CH:39]([C:36]3[CH:37]=[CH:38][C:33]([CH2:30][CH2:31][CH3:32])=[CH:34][CH:35]=3)[CH2:44][CH2:43]2)[CH2:46][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 59408364HCID 59408364, compound

Product 1

HCID 59408345HCID 59408345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 55.0 g (0.50 mol) of potassium tert-butoxide in 250 ml of THF is added to a suspension of 170.0 g (0.50 mol) of methoxymethyltriphenylphosphonium chloride in 550 ml of THF at 0° C. After 30 min at this temperature, a solution of 4′-(4-propylphenyl)bicyclohexyl-4-one in 450 ml of THF is added, and the mixture is stirred at room temperature for 17 h. Water is added to the batch, which is then acidified using hydrochloric acid. The mixture is extracted a number of times with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is concentrated to completion, and the residue is purified by column chromatography (SiO2, n-heptane:MTBE=8:1).

Workup

  1. extractionThe mixture is extracted a number of times with MTBE
  2. washthe combined organic phases are washed with water and saturated sodium chloride solution
  3. concentrationThe solution is concentrated to completion
  4. customthe residue is purified by column chromatography (SiO2, n-heptane:MTBE=8:1)

Sources & evidence

ORD record
ord-fd96e281c7024bea92746b9edf9f909d
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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