Sulfuric Acid → HCID 178460681, compound

HRID 2090119Notes

Reaction equation

HRID 2090119 reaction equation
O.[PH2:2]([O-:4])=[O:3].[Na+].S(=O)(=O)(O)O.[CH3:11][C:12]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH2:13].CC(N=NC(C#N)(C)C)(C#N)C>CC(N=NC(C#N)(C)C)(C#N)C.C(O)C>[CH3:11][CH:12]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:13][PH:2](=[O:4])[OH:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6547AzobisisobutyronitrileHCID 78682,4,4-Trimethyl-1-penteneHCID 178418950HCID 178418950, compound

Product 1

HCID 178460681HCID 178460681, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 702EthanolSolvent

Procedure

A 2 L 4-neck flask, equipped with thermocouple well, a dropping funnel, overhead stirrer and reflux condenser is charged with 199 grams (1.88 moles) of sodium hypophosphite monohydrate and 500 mL of 2B ethanol. Into the resultant stirred suspension is added via the dropping funnel, 52 mL (1.87 moles) of concentrated sulfuric acid. During the addition the reaction mixture temperature rises from 21° C. to 27° C. After approximately 15 minutes, 100 mL (0.624 moles) of 2,4,4-trimethyl-1-pentene is added, followed by 10.24 g (0.062 moles) of AIBN powder. The reaction mixture is heated at reflux under a nitrogen atmosphere for 20 hours. An additional 6.84 g (0.042 moles) of AIBN powder is added and the mixture is refluxed under nitrogen for another 20 hours. Solvent is removed under vacuum and the residue is partitioned between 400 mL heptane and 1 L of water. The heptane layer is concentrated under vacuum to give 98 grams (88% of theory) of 2,4,4-trimethylpentyl phosphinic acid as a colorless oil.

Workup

  1. customA 2 L 4-neck flask, equipped with thermocouple well, a dropping funnel
  2. temperatureoverhead stirrer and reflux condenser
  3. additionDuring the addition the reaction mixture temperature
  4. customrises from 21° C. to 27° C
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux under a nitrogen atmosphere for 20 hours
  7. temperaturethe mixture is refluxed under nitrogen for another 20 hours
  8. customSolvent is removed under vacuum
  9. customthe residue is partitioned between 400 mL heptane and 1 L of water
  10. concentrationThe heptane layer is concentrated under vacuum

Sources & evidence

ORD record
ord-98b5b13385604a4f8355d4ee4cf67cdd
Source dataset
uspto-grants-2013_05
Patent number
US08436131B2

Reaction notes

Loading…