Water → HCID 57218863, compound

HRID 224746Notes

Reaction equation

HRID 224746 reaction equation
CN(P(N(C)C)N(C)C)C.[CH3:11][O:12][CH:13]([O:22][CH3:23])[CH2:14][C@@H:15]1[C:17]([CH3:19])([CH3:18])[C@@H:16]1[CH:20]=O.[C:24](Cl)(Cl)([Cl:26])[Cl:25].O>CCCCC>[CH3:11][O:12][CH:13]([O:22][CH3:23])[CH2:14][C@H:15]1[C:17]([CH3:19])([CH3:18])[C@H:16]1[CH:20]=[C:24]([Cl:26])[Cl:25]

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 15355Hexamethylphosphorous triamideHCID 54422830HCID 54422830, compound

Product 1

HCID 57218863HCID 57218863, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
14 °C

Procedure

Tri(dimethylamino)phosphine (163.2 mmol) was added with stirring at 0° C. to a solution of (1R,cis)-2-(2,2-dimethoxyethyl)-3,3-dimethylcyclopropanecarbaldehyde (65.5 mmol) and carbon tetrachloride (163.2 mmol) in n-pentane (350 ml) kept under nitrogen in a 1-l flask. After 15 minutes stirring, the mixture was warmed up to 14° C. and kept at this temperature for 15 minutes. Then, water (75 ml) was added at 14° C. and--after removal of the aqueous phase--the organic phase was washed with two 35-ml portions of water. The washed organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried solution to give a residue (15.7 g) containing 32.1 mmol of 2-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]ethanal dimethyl acetal (100% (1R,cis), purity 51.7%, yield 49%).

Workup

  1. customkept under nitrogen in a 1-l flask
  2. waitkept at this temperature for 15 minutes
  3. custom--after removal of the aqueous phase
  4. washthe organic phase was washed with two 35-ml portions of water
  5. dry with materialThe washed organic phase was dried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated from the dried solution

Sources & evidence

ORD record
ord-c724c0d80e6047478c23df3f9a5e98d7
Source dataset
uspto-grants-1980_11
Patent number
US04234512

Reaction notes

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