Methanol → HCID 13344136, compound

HRID 261458Notes

Reaction equation

HRID 261458 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4]([CH2:5][C:6]([Cl:9])([Cl:8])Cl)[CH:3]1[C:10]([O:12]C)=[O:11].[OH-].[Na+].[CH3:17]O>>[CH3:17][C:3]1([C:10]([OH:12])=[O:11])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:9])[C:2]1([CH3:1])[CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11557959Methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate2×

Product 1

HCID 13344136HCID 13344136, compoundYield 78%

Procedure

A mixture of 9.0 g (0.035 mole) of methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate (compound Z, C/T=75/25) in 30 ml of a 20% aqueous solution of sodium hydroxide (0.15 mole) and 10 ml of methanol was heated to 98° over 30 minutes. Heating was continued at this temperature for 5 hours. The reaction mixture was cooled, washed with ether, and the aqueous phase made acidic by the addition of concentrated hydrochloric acid. The acidic mixture was extracted with ether, and the ether extracts were combined, washed with brine, dried over magnesium sulfate, and concentrated to give, after distillation, 5.68 g (78% yield) of methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid, the acid corresponding to compound C, 95% purity, C/T=78/22.

Workup

  1. temperaturewas heated to 98° over 30 minutes
  2. temperatureHeating
  3. temperatureThe reaction mixture was cooled
  4. washwashed with ether
  5. additionthe aqueous phase made acidic by the addition of concentrated hydrochloric acid
  6. extractionThe acidic mixture was extracted with ether
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give

Sources & evidence

ORD record
ord-d2df0bbf28b44efab4d398cd350f7802
Source dataset
uspto-grants-1979_08
Patent number
US04166064

Reaction notes

Loading…