Thionyl Chloride → HCID 21510426, compound

HRID 1576954Notes

Reaction equation

HRID 1576954 reaction equation
O[CH2:2][CH:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][CH2:2][CH:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21510427HCID 21510427, compound

Product 1

HCID 21510426HCID 21510426, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxy-2-phenoxy-4,4-dimethyl-pentan-3-one (111.1 g, 0.5 mol) is dissolved in 500 ml of methylene chloride. Thionyl chloride (62 g, 0.52 mol) is added dropwise to the solution at room temperature. The start of the reaction can be accelerated by gentle warming. After a reaction time of two hours at room temperature, the solvent is distilled off in vacuo and the oily residue is degassed in a high vaccum to afford 93.0 g (77% of theory) of 1-chloro-4,4-dimethyl-2-phenoxy-pentan-3-one as an oil having a refractive index of nD20 = 1.5081 and a boiling point of (0.4 mm Hg)/110°C.

Workup

  1. customThe start of the reaction
  2. distillationAfter a reaction time of two hours at room temperature, the solvent is distilled off in vacuo
  3. customthe oily residue is degassed in a high vaccum

Sources & evidence

ORD record
ord-f28347fb705c4ccebb12293f5a2fa7dc
Source dataset
uspto-grants-1976_09
Patent number
US03983240

Reaction notes

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