Aluminum(III) Chloride → HCID 59211734, compound

HRID 1175656Notes

Reaction equation

HRID 1175656 reaction equation
[CH2:1]([C:6]1([CH:13]=[O:14])[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH3:5].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([CH:6]1[CH2:11][CH:10]2[CH2:9][CH:8]([CH:7]=[CH:12]2)[C:13]1=[O:14])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59211737HCID 59211737, compound

Product 1

HCID 59211734HCID 59211734, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Pentylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (217 g, synthesized as above) was loaded into a 2-L round bottom flask fitted with an overheard stirrer and a condenser, followed by CH2Cl2 (1 L). The resulting mixture was cooled to 0° C. using a dry ice bath. AlCl3 (153 g) was then added in one portion. After GC analysis showed the completion of the reaction, the reaction mixture was poured onto ice, and the organic layers were separated and washed once with sodium hydroxide solution (10%). The solvent (CH2Cl2) was then removed under reduced pressure, and the resulting crude product was purified by distillation to yield 3-pentylbicyclo[3.2.1]oct-6-en-2-one (100 g).

Workup

  1. customfitted with an overheard stirrer and a condenser
  2. customthe completion of the reaction
  3. additionthe reaction mixture was poured onto ice
  4. customthe organic layers were separated
  5. washwashed once with sodium hydroxide solution (10%)
  6. customThe solvent (CH2Cl2) was then removed under reduced pressure
  7. distillationthe resulting crude product was purified by distillation

Sources & evidence

ORD record
ord-5736d120149a4a53b41c084bc593b2e2
Source dataset
uspto-grants-2010_11
Patent number
US07842659B2

Reaction notes

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