Methanol → HCID 67957891, compound

HRID 1475674Notes

Reaction equation

HRID 1475674 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]2)[CH2:9][CH3:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].S(Cl)(Cl)=O.[CH3:24]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2([C:14]([O:16][CH3:24])=[O:15])[CH2:12][CH2:13]2)[CH2:9][CH3:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67957780HCID 67957780, compound

Product 1

HCID 67957891HCID 67957891, compound

Conditions

Temperature
0 °C

Procedure

262 mg (about 0.93 mmol) of 1-[1-(4-chloro-3-nitrophenyl)propyl]cyclopropanecarboxylic acid were dissolved in 5 ml of methanol, the mixture was cooled to 0° C. and 0.14 ml (1.85 mmol) of thionyl chloride was added dropwise. The reaction solution was then slowly warmed to room temperature and stirred at this temperature overnight. The reaction mixture was then concentrated to dryness and the residue was taken up in 10 ml of dichloromethane. The solution was washed with water, dried over magnesium sulphate and concentrated under reduced pressure. This gave 224 mg of the target compound (81% of theory).

Workup

  1. temperatureThe reaction solution was then slowly warmed to room temperature
  2. concentrationThe reaction mixture was then concentrated to dryness
  3. washThe solution was washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f87d1e1b9b2c4fedaafa897add8a13a1
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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