Dichloromethane → 1-(1-Chloro-ethyl)-2-chloromethyl-benzene

HRID 2094715Notes

Reaction equation

HRID 2094715 reaction equation
OC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9](O)[CH3:10].S(Cl)([Cl:14])=O.[CH2:16]([Cl:18])Cl>>[Cl:14][CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:16][Cl:18])[CH3:10]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 5769111-(2-(Hydroxymethyl)phenyl)ethanol

Product 1

HCID 670767721-(1-Chloro-ethyl)-2-chloromethyl-benzene

Procedure

1-(2-Hydroxymethyl-phenyl)-ethanol (prepared according to the procedure described in P. Canorme et al., Tetrahedron 44 (1988), 2903-2912) (0.376 g, 2.47 mmol) was dissolved in DCM. Thionyl chloride (2.94 g, 24 mmol) was added and allowed to react for 1 h. The mixture was partitioned between EA and an excess of an aqueous sodium hydrogencarbonate solution. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography with HEP to yield 0.228 g of the title compound.

Workup

  1. customto react for 1 h
  2. customThe mixture was partitioned between EA
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by silica gel chromatography with HEP

Sources & evidence

ORD record
ord-1a0579ab13da4dd3a602ba7e4a013d49
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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