Hydrochloric Acid → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethanone

HRID 1393048Notes

Reaction equation

HRID 1393048 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([O:21][Si](C)(C)C)[C:19]#N)=[CH:14][CH:13]=1.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1CCl.Cl.[OH-].[K+]>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][C:30]2[CH:29]=[CH:28][C:27]([Cl:26])=[CH:32][C:31]=2[Cl:33])=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 72122,4-Dichlorobenzyl chlorideHCID 14797Potassium HydroxideHCID 2733832Lithium HexamethyldisilazideHCID 10776410HCID 10776410, compound

Product 1

HCID 5872691-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

32 g of LiHMDS are placed in 245 ml of THF at 0° C., and 40 g of (4-chlorophenyl) ((trimethylsilyl)oxy)acetonitrile are added slowly at −78° C., followed by 32.64 g of 2,4-dichloro-1-(chloromethyl)benzene. The temperature is allowed to return to AT overnight, and the reaction is then hydrolyzed with 170 ml of a 3N HCl solution, with gases being trapped in a solution of KOH (4N). After separation by settling out, the organic phase is evaporated, then taken up in DCM and agitated for 1 hour with 170 ml of NaOH (2N). The DCM is evaporated off and the expected compound is then crystallized from pentane. 38.6 g are obtained, Mp=119° C.

Workup

  1. customto return to AT overnight
  2. customAfter separation
  3. customthe organic phase is evaporated
  4. customThe DCM is evaporated off
  5. customthe expected compound is then crystallized from pentane
  6. custom38.6 g are obtained

Sources & evidence

ORD record
ord-bdced96221254e0ab572be46a89cd471
Source dataset
uspto-grants-2008_03
Patent number
US07345059B2

Reaction notes

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