Acetic Acid → HCID 68568445, compound

HRID 747605Notes

Reaction equation

HRID 747605 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.C([Li])CCC.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:23]([O-:25])=[O:24])=[C:19]([CH:22]=1)[CH:20]=[O:21].C(O)(=O)C>C1COCC1.CCCCCC>[N+:23]([C:18]1[CH:17]=[CH:16][C:15]([Cl:14])=[CH:22][C:19]=1[CH:20]([C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[OH:21])([O-:25])=[O:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 109431,3-DichlorobenzeneHCID 811235-Chloro-2-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 68568445HCID 68568445, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 16.75 g of 1,3-dichlorobenzene dissolved in 250 ml of THF are added dropwise, at −70° C., 68 ml of a 1.6M solution in hexane of n-butyllithium. After one hour at −70° C., 10 g of 5-chloro-2-nitrobenzaldehyde dissolved in THF are introduced and the mixture is left for 3 hours at this temperature. The resulting mixture is hydrolysed by addition of 5 ml of acetic acid and is allowed to warm to room temperature. The resulting mixture is concentrated and the residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture to give 7.975 g of the expected product.

Workup

  1. additionare added dropwise, at −70° C.
  2. additionare introduced
  3. waitthe mixture is left for 3 hours at this temperature
  4. concentrationThe resulting mixture is concentrated
  5. customthe residue is chromatographed on a column of silica gel
  6. washeluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-30ac8eb515234d6e9040a57f9b59ddde
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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