Sulfuric Acid → HCID 59211735, compound

HRID 2243792Notes

Reaction equation

HRID 2243792 reaction equation
[CH2:1]([C:7]1([CH:14]=[O:15])[CH2:12][CH:11]2[CH2:13][CH:8]1[CH:9]=[CH:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:1]([CH:7]1[CH2:12][CH:11]2[CH2:10][CH:9]([CH:8]=[CH:13]2)[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 57740814HCID 57740814, compound

Product 1

HCID 59211735HCID 59211735, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-30 °C

Procedure

Compound XII (236 g, 1.1 mol) was loaded into a three liter flask and dissolved in one liter of toluene. This mixture was then cooled to −30° C. Aluminum chloride (77 g, 0.56 mol) was then added in one portion. The reaction mixture exothermed moderately and changed color to light orange. The temperature was allowed to rise to −15° C., then held for 3.5 hours. After this time the reaction was complete as shown by GC measurements. The reaction mixture was then poured onto ice and 25% sulfuric acid, and the organic layers were separated and washed once with 10% sodium hydroxide solution. The methylene chloride solvent was then removed under reduced pressure, and the resulting oil was purified by simple distillation to yield 163 g (69% yield) of XIII.

Workup

  1. customto rise to −15° C.
  2. customthe organic layers were separated
  3. washwashed once with 10% sodium hydroxide solution
  4. customThe methylene chloride solvent was then removed under reduced pressure
  5. distillationthe resulting oil was purified by simple distillation

Sources & evidence

ORD record
ord-52085ee27faf4094822d13412647e0b4
Source dataset
uspto-grants-2010_03
Patent number
US07678749B2

Reaction notes

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