Dichloromethane → 4,4'-Dichlorobenzhydryl chloride

HRID 359392

Reaction equation

HRID 359392 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([CH:10](O)[C:11]2[CH:16]=[CH:15]C=[CH:13][CH:12]=2)=[CH:8][CH:7]=1.[CH2:20]([Cl:22])Cl>>[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([CH:10]([C:11]2[CH:16]=[CH:15][C:20]([Cl:22])=[CH:13][CH:12]=2)[Cl:3])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 84014-ChlorobenzhydrolHCID 24386Thionyl Chloride

Product 1

HCID 130784,4'-Dichlorobenzhydryl chlorideYield 88.4%

Procedure

Thionyl chloride (10 mL, 137 mmol) was added dropwise to 4-chlorobenzhydrol (12.66 g, 50 mmol) in CH2Cl2 (200 mL) under nitrogen over 15 min. After 18 h and solvent removal in vacuo, the crude product was dissolved in methylene chloride (250 mL) and washed with saturated NaHCO3 (3×50 mL), dried over Na2SO4, and concentrated in vacuo to a thin, amber oil (12.53 g). Upon standing at room temperature for 1 h, crystallization occured to give pure product (12.5 g, 88.4%) as a white solid, mp 61°-64° C. DCI/MS (M+1) 235. 400 MHz 1H NMR (CDCl3) δ: 7.35 (m, 8H), 6.05 (s, 1H).

Workup

  1. customsolvent removal in vacuo
  2. dissolutionthe crude product was dissolved in methylene chloride (250 mL)
  3. washwashed with saturated NaHCO3 (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to a thin, amber oil (12.53 g)
  6. waitUpon standing at room temperature for 1 h
  7. customcrystallization

Sources & evidence

ORD record
ord-4f45f472fee743ea8fe9527ea520342d
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Linked notes

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