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

HRID 21682

Reaction equation

HRID 21682 reaction equation
[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([OH:20])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]12CC3CC(CC(CC(OC)=O)(C3)C1)C2.[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1>[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:22])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 610084HCID 610084, compoundHCID 2771107(3-Phenyl-1-adamantyl)acetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53665692Methyl 3-phenyl-1-adamantaneacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Preparation of 3-Phenyl-l-adamantaneacetic acid, a hapten. 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-4e36a21ee6d845b586893d9fe90a7e86
Source dataset
uspto-grants-1995_06
Patent number
US05424414

Linked notes

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