p-Xylyl bromide → HCID 22990062, compound

HRID 1169319Notes

Reaction equation

HRID 1169319 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CN(C=O)C>[CH3:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:1][C:2]2[CH:13]=[CH:12][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=3[CH:3]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 2295073-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

Product 1

HCID 22990062HCID 22990062, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (1.76 g, 10.0 mmol) dissolved in DMF (10 ml) were added potassium carbonate (2.76 g, 20.0 mmol) and 4-methylbenzyl bromide (2.04 g, 11.0 mmol), and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with water (20 ml) and extracted with ethyl acetate (20 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 40 g, ethyl acetate/hexane=1/30). The objective fractions were concentrated under reduced pressure to obtain 3-(4-methylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.74 g, 9.77 mmol, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was mixed with water (20 ml)
  3. extractionextracted with ethyl acetate (20 ml×3)
  4. dry with materialThe combined organic layers were dried with anhydrous magnesium sulfate
  5. concentrationwere then concentrated under reduced pressure
  6. concentrationThe objective fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf545804ba4b47a0a1e3256006012525
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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