Hydrochloric Acid → 1-Allyl-2-(benzyloxy)benzene

HRID 322020Notes

Reaction equation

HRID 322020 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=O.[Li+].[Cl-].[Li][O:16][C:17]([CH3:19])=O.Cl>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:4]([C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[O:16][CH2:17][C:19]1[CH:11]=[CH:12][CH:2]=[CH:3][CH:4]=1)[CH:5]=[CH2:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1013463-(2-Bromophenyl)prop-2-enoic acidHCID 433294Lithium ChlorideHCID 178506943lithium acetate

Product 1

HCID 114701341-Allyl-2-(benzyloxy)benzene

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture containing 2-bromocinnamic acid (250 mg, 1.10 mmol), the product of step 1 (271 mg, 1.1 equiv.), Pd(OAc)2 (8 mg, 0.03 equiv.), LiCl (47 mg, 1 equiv.), LiOAc (280 mg, 2.5 equiv.) and Bu4NCl (611 mg, 2 equiv.) in DMF (2 ml) was degassed and heated to 100 C. o.n. 0.5 N HCl was then added and the product was extracted in EtOAc, washed with 0.5 N HCl, dried over Na2SO4 and concentrated to dryness. Recrystallization from ether:hexane afforded the title product as a white solid. Yield: 251 mg, 62%.

Workup

  1. temperatureheated to 100 C
  2. extractionthe product was extracted in EtOAc
  3. washwashed with 0.5 N HCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customRecrystallization from ether

Sources & evidence

ORD record
ord-a084985d827742d68ce90a6f98e1bb15
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

Loading…