HCID 610084, compound → Methyl 3-phenyl-1-adamantaneacetate

HRID 51983

Reaction equation

HRID 51983 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH2:5]3)[CH2:3]1)[CH2:9]2.[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1>[C:2]1([C:2]23[CH2:11][CH:6]4[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH2:5]4)[CH2:3]2)[CH2:9]3)[CH:11]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 610084HCID 610084, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53665692Methyl 3-phenyl-1-adamantaneacetateYield 202%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 3-bromoadamantaneacetate (80 g) (Aldrich Chemical Co. Milwaukee Wis.) was dissolved in benzene (1.6 L) under nitrogen. Aluminum trichloride (37.12 g) was added portionwise over 75 min. at ambient temperature. The reaction mixture was then quenched by the addition of 0.5M phosphoric acid (1.6 L). The layers were separated and the organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to give methyl 3-phenyl-1-adamantaneacetate (80 g).

Workup

  1. customThe reaction mixture was then quenched by the addition of 0.5M phosphoric acid (1.6 L)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-33797f736a214462ba6cf92a008f2560
Source dataset
uspto-grants-1997_04
Patent number
US05616505

Linked notes

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