Thionyl Chloride → HCID 14068957, compound

HRID 1904778Notes

Reaction equation

HRID 1904778 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH:7](O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([O-:3])=[O:2].S(Cl)([Cl:19])=O>N1C=CC=CC=1>[Cl:19][CH:7]([C:6]1[CH:14]=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14068956HCID 14068956, compound

Product 1

HCID 14068957HCID 14068957, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A mixture of 97 g of ethyl 3-nitromandelate and 69 ml of thionyl chloride is stirred overnight at room temperature. Then a few drops of pyridine are added. After the evolution of gas has ceased, the mixture is stirred for about 2 hours at 100° C. Excess thionyl chloride is evaporated off in a water jet vacuum and the reaction mixture is distilled in a high vacuum. The title compound (b) is obtained in the form of a yellow oil with b.p. 134° C. at 0.06 mbar and with an Rf value of 0.5 on thin-layer silica gel plates in a methylene chloride system.

Workup

  1. stirringthe mixture is stirred for about 2 hours at 100° C
  2. customExcess thionyl chloride is evaporated off in a water jet vacuum
  3. distillationthe reaction mixture is distilled in a high vacuum

Sources & evidence

ORD record
ord-2c51ff074b804a32ab4a9220863010a0
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

Loading…