Hydrochloric Acid → HCID 6713300, compound

HRID 1870778Notes

Reaction equation

HRID 1870778 reaction equation
Cl.[CH3:2][C:3]([CH3:9])([C:5](=[O:8])[CH2:6][CH3:7])[CH3:4].[N:10](OCCCC)=[O:11]>C(OCC)C.C1(C)C=CC=CC=1>[OH:11][N:10]=[C:6]([CH3:7])[C:5](=[O:8])[C:3]([CH3:9])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 1363632,2-Dimethyl-3-pentanone

Product 1

HCID 6713300HCID 6713300, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 40 g of hydrogen chloride in 156 g of diethyl ether is added dropwise at room temperature to 96 g (0.84 mol) of 2,2-dimethyl-3-pentanone in 960 g of toluene. After cooling to -10° C., a solution of 95 g of n-butyl nitrite in 470 g of diethyl ether is added dropwise. The mixture is stirred at from -10° C. to 0° C. for 4 hours and then allowed to come to room temperature. After a total of 16 h, the reaction mixture is washed three times with 1 l of ice-water each time and then extracted twice with 1 l of 1M sodium hydroxide solution each time. The alkaline phase is separated off and neutralized with 20% strength sulfuric acid. The crude product is filtered off with suction and, after drying, recrystallized from n-hexane. 66 g (55%) of the title compound are obtained as a pale yellow powder of melting point 107-110° C.

Workup

  1. customto come to room temperature
  2. washAfter a total of 16 h, the reaction mixture is washed three times with 1 l of ice-water each time
  3. extractionextracted twice with 1 l of 1M sodium hydroxide solution each time
  4. customThe alkaline phase is separated off
  5. filtrationThe crude product is filtered off with suction
  6. customafter drying
  7. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-7cb502043b23486cb3dff66aa04005a9
Source dataset
uspto-grants-2000_08
Patent number
US06100263

Reaction notes

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