Hexane → HCID 12037344, compound

HRID 1639734Notes

Reaction equation

HRID 1639734 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=[CH2:3].[C:12](=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][CH:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29]C=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:31]1[CH:32]=[CH:27][C:26]([O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:29][CH:30]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 2584682-ALLYL-4-BROMOPHENOL2×HCID 21972261HCID 21972261, compound

Product 1

HCID 12037344HCID 12037344, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere replaced with argon, 2-allyl-4-bromophenol (compound 3), potassium carbonate and benzyloxy-benzylchloride (BnBr) were dissolved in dimethylformamide (DMF), and stirred at room temperature for 3 hours. After confirming that the starting materials were disappeared using thin-layer chromatography (TLC) (with a developer of n-hexane:ethyl acetate=4:1), the reaction liquid was subjected to extraction using 20 mL of water and 20 mL of ethyl acetate. The organic phase was washed with 20 mL of water twice, dried using magnesium sulfate, and then subjected to filtration. The filtrate was concentrated under reduced pressure using an evaporator. The resultant residue was subjected to purification using silica gel flash chromatography (silica gel flash c.c.) (with a developer of n-hexane:ethyl acetate×4:1), to thereby obtain 2-allyl-1-(4-benzyloxy-benzyloxy)-4-bromobenzene (compound 4) as light brown solid.

Workup

  1. extractionwas subjected to extraction
  2. washThe organic phase was washed with 20 mL of water twice
  3. customdried
  4. filtrationsubjected to filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customan evaporator
  7. customThe resultant residue was subjected to purification

Sources & evidence

ORD record
ord-5782abed08dd4c178da8be4447310698
Source dataset
uspto-grants-2012_02
Patent number
US08110601B2

Reaction notes

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