Tetralin → 2-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one

HRID 271797Notes

Reaction equation

HRID 271797 reaction equation
[CH3:1][C:2]([C:4](Cl)=[O:5])=[CH2:3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1>C(Cl)Cl>[CH3:1][CH:2]1[C:4](=[O:5])[C:13]2=[CH:14][C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[CH:11]=[C:12]2[CH2:3]1

Participants

5

Reactant 3

HCID 8404TetralinHCID 13528Methacryloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 224992222-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methacryl chloride (37.5 ml, 375 mmol) was added at −70° C. to well-stirred suspension of AlCl3 (100 g, 750 mmol) in CH2Cl2 (600 ml). After 20 min tetrahydronaphthalene (49.5 g, 375 mmol) was added. Reaction mixture was allowed to warm to room temperature, stirred for 16 h and poured into ice water-HCl (1 l/150 ml). Organic layer was separated, water layer was extracted by CH2Cl2 (2100 ml). Combined organic phases were washed by water, aq. NaHCO3, dried over MgSO4 and evaporated. Vacuum distillation (130-140° C./0.5 Torr) a mixture of ketones. After storage within 5 days desired isomer stays liquid and can be separated by decantation. The yield 30 g (40%).

Workup

  1. customReaction mixture
  2. stirringstirred for 16 h
  3. customOrganic layer was separated
  4. extractionwater layer was extracted by CH2Cl2 (2100 ml)
  5. washCombined organic phases were washed by water, aq. NaHCO3
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. distillationVacuum distillation (130-140° C./0.5 Torr)
  9. additiona mixture of ketones
  10. customliquid and can be separated by decantation

Sources & evidence

ORD record
ord-6f1cdeff789e45b29987184f36fa4862
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

Loading…