Sodium Hydroxide → 8-Bromo-2-methoxy-1-methyl-11,12-dihydro-6H-dibenzo[a,e]cycloocten-5-one

HRID 730178Notes

Reaction equation

HRID 730178 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[CH3:22])=[C:6]([CH2:8][C:9](O)=O)[CH:7]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-:37].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH2:13][C:14]3[C:15]([CH3:22])=[C:16]([O:20][CH3:21])[CH:17]=[CH:18][C:19]=3[C:9](=[O:37])[CH2:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 578344835-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylacetic acid

Product 1

HCID 578344888-Bromo-2-methoxy-1-methyl-11,12-dihydro-6H-dibenzo[a,e]cycloocten-5-oneYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 5-bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetic acid (11) (4.38 g; 12.06 mmol) in toluene (20 mL), was added phosphorous pentoxide (6.0 g; 42.2 mmol). The mixture was heated at 90° C. for 16 hours. The mixture was cooled, treated with 1.0 N solution of sodium hydroxide and extracted with chloroform. The extracts were combined, dried over Na2SO4, and evaporated. The resultant residue was chromatograped on silica gel using hexane and ethyl acetate (4:1) to give compound 12 as colorless crystals, 2.40 g; 55% yield.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with chloroform
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-a6a6bbf923804f2bab6d4ab535f31f06
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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