Thioanisole → HCID 18183648, compound

HRID 1358164Notes

Reaction equation

HRID 1358164 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:13](Cl)(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([C:13](=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([C:4]2[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=2)=[O:22])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 67165Nonanedioyl dichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18183648HCID 18183648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thioanisole (23.5 ml, 0.20 mol) is added to a suspension of AlCl3 (27.3 g, 0.205 mol) in 200 ml of CH2Cl2. Azelaoyl chloride (19.7 ml, 0.10 mol) is added dropwise slowly, while the reaction mixture is cooled in an ice bath and the reaction solution is stirred for 19 h at room temperature. Then, the reaction solution is poured into ice-water. The produced white precipitate is filtered off and the crude product is extracted from the filtrate with CH2Cl2, washed with brine, dried over MgSO4, and concentrated. The residue is purified by recrystallization from i-Pr2O—CHCl3. The product is obtained as a white solid. 1H NMR (CDCl3), δ[ppm]: δ1.35-1.43 (m, 6H), 1.72 (t, 4H), 2.52 (s, 6H), 2.91 (t, 4H), 7.26 (d, 4H), 7.87 (d, 4H)

Workup

  1. temperatureis cooled in an ice bath
  2. filtrationThe produced white precipitate is filtered off
  3. extractionthe crude product is extracted from the filtrate with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallization from i-Pr2O—CHCl3
  8. customThe product is obtained as a white solid

Sources & evidence

ORD record
ord-1a3f8dce87414f3e8ab420e2cca79879
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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