Sulfuric Acid → HCID 59211738, compound

HRID 2243789Notes

Reaction equation

HRID 2243789 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:12]1([CH:19]=[O:20])[CH2:17][CH:16]2[CH2:18][CH:13]1[CH:14]=[CH:15]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].S(=O)(=O)(O)O>C(Cl)Cl>[CH2:5]([CH:12]1[CH2:17][CH:16]2[CH2:15][CH:14]([CH:13]=[CH:18]2)[C:19]1=[O:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6451240Aluminum(III) ChlorideHCID 57740812HCID 57740812, compound

Product 1

HCID 59211738HCID 59211738, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (279 g, 2 mol) was dissolved in one liter of methylene chloride in a three liter flask and cooled to 0° C. Structure III (909 g, 4.1 mol) was loaded into an addition funnel and fed into the reaction flask while maintaining this temperature. After two hours the reaction was complete as shown by GC measurements. The reaction mixture was then poured onto ice and 10% 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 260 g (28% yield) of IV. Structure IV, 3-heptylbicyclo[3.2.1]oct-6-en-2-one, possesses weak, methyl salicylate like and slightly fruity fragrance notes.

Workup

  1. temperaturewhile maintaining this temperature
  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-87460dc363db484d845a69797c752a30
Source dataset
uspto-grants-2010_03
Patent number
US07678749B2

Reaction notes

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