Hydrochloric Acid → 2-Propanone, 1-(2-nitrophenoxy)-

HRID 1373355

Reaction equation

HRID 1373355 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Cl[CH2:12][C:13](=[O:15])[CH3:14].[Br-].[Na+].C(=O)(O)[O-].[Na+].Cl>[Cl-].C([N+](CCCC)(CCCC)C)CCC.O.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:12][C:13](=[O:15])[CH3:14])([O-:3])=[O:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6571Chloroacetone2×HCID 69472-NitrophenolHCID 253881Sodium BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 792392-Propanone, 1-(2-nitrophenoxy)-

Reagents, catalysts & solvents 3

HCID 91822Tributylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

The o-nitrophenoxyacetone is prepared by heating with agitation for five hours at about 65° C. a mixture which consists of 421.6 g (3.006 moles) of o-nitrophenol, 297.8 g (3.09 moles) of chloroacetone, 37.2 g (96%, 0.3615 moles) of sodium bromide, 277.2 g (3.3 moles) of sodium bicarbonate, 21.8 g (0.0647 moles) of aqueous tributylmethylammonium chloride (TBMAC), and 829 g of toluene. There is then added 9.0 g (0.093 mole) of additional chloroacetone to the mixture which is further heated at 65° C. for 2.5 hours (note, sample analysis indicated that the reaction was complete after 1.5 hours). There is then added, 570 g of water and the pH of the mixture is adjusted to 6.5–7 at 55° C. to 60° C. upon addition of 55 g of a 10% HCl solution. The phases are allowed to separate and the aqueous phase is removed.

Workup

  1. temperatureis further heated at 65° C. for 2.5 hours (note, sample analysis
  2. additionThere is then added
  3. customto separate
  4. customthe aqueous phase is removed

Sources & evidence

ORD record
ord-c1a0ca114e1f4ca7881d65a3e76d38d5
Source dataset
uspto-grants-2007_01
Patent number
US07161001B2

Linked notes

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