Water → HCID 21107221, compound

HRID 1869902Notes

Reaction equation

HRID 1869902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12]C)[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 21107223HCID 21107223, compound2×

Product 1

HCID 21107221HCID 21107221, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (ice bath) solution of 6-bromo-8-methoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 64, 0.24 g, 0.83 mmol) in anhydrous dichloromethane (4 mL) was treated with aluminum chloride (0.4 g, 3 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. It was poured into water and extracted with dichloromethane and ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a brown oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title product as a pale yellow solid (0.13 g, 56%).

Workup

  1. extractionextracted with dichloromethane and ethyl acetate
  2. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a brown oil that

Sources & evidence

ORD record
ord-f669aa32c8244c40b168b064c2a87c59
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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