Formaldehyde → 2-(Phenylselenyl)ethoxylmethyl chloride

HRID 1555Notes

Reaction equation

HRID 1555 reaction equation
[C:1]1([Se:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[CH2:13](Cl)[Cl:14]>>[C:1]1([Se:7][CH2:8][CH2:9][O:10][CH2:13][Cl:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 11030856Ethanol, 2-(phenylseleno)-

Product 1

HCID 146300942-(Phenylselenyl)ethoxylmethyl chloride

Procedure

To a solution of 2-(phenylselenyl)ethanol (4.0 g, 20 mmol) [prepared according to the literature procedure: P. Rollin, V. V. Bencomo, P. Sinay, Synthesis, 13 (1984)] in CH2Cl2 (15 mL) was added paraformaldehyde (620 mg, 20 mmol). HCl gas was then bubbled into the solution at 5° C. for 2 hr. The solution was dried (MgSO4), and the solvent was removed under reduced pressure to give the title compound as a colorless oil in a quantitative yield.

Workup

  1. customHCl gas was then bubbled into the solution at 5° C. for 2 hr
  2. dry with materialThe solution was dried (MgSO4)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e7425b3ba2444f079944b9d7bd609176
Source dataset
uspto-grants-1998_03
Patent number
US05726174

Reaction notes

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