Methanol → HCID 13657591, compound

HRID 1608241Notes

Reaction equation

HRID 1608241 reaction equation
Br[C:2]1([C:13]([C:15]2(Br)[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]2CCCCl)=[O:14])[CH:7]=[CH:6]C(Cl)=CC1CCCCl.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1.CO>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]([C:2]2([O:40][C:37]3[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=3)[CH2:7][CH2:6]2)=[O:14])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 86743404HCID 86743404, compound

Product 1

HCID 13657591HCID 13657591, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 14.8 g=50 mmol of 1-bromo-3-chloropropyl4-chlorophenyl ketone in 30 ml of acetonitrile was added dropwise at room temperature with stirring to a suspension of 17.2 g=125 mmol of powdered potassium carbonate and 6.4 g=50 mmol of p-chlorophenol in 60 ml of acetonitrile. The mixture was stirred for 5 hours at room temperature, 0.4 g of tetrabutylammonium bromide was added, and the mixture was refluxed for 10 hours and worked up as specified in Example 1, and 12.6 g (82% of theory) of melting point: 69°-71° C. (from methanol) were obtained.

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. customwere obtained

Sources & evidence

ORD record
ord-02b6c7ab92d241cf8e9729fa3f4c8f20
Source dataset
uspto-grants-1989_09
Patent number
US04870088

Reaction notes

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