Dichloromethane → Chavicol

HRID 1419932Notes

Reaction equation

HRID 1419932 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10]C)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C(Cl)Cl>>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 8815Estragole

Product 1

HCID 68148ChavicolYield 89%

Procedure

To a -78° C. cold solution of 4-allylanisol (14.6 ml, 95 mmol) in CH2Cl2 (300 ml) BBr3 (100 ml, 0.1 mol, 1 mol/l in CH2Cl2) was added dropwise. The reaction mixture was then allowed to warm up to room temperature. After 1 hour, the reaction mixture was cooled to 0° C. and quenched slowly with H2O (90 ml). The resulting aqueous phase was extracted with CH2Cl2 (2×100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 9:1) to provide 4-allylphenol (11.3 g, 89%) as a purple oil, MS: m/e=134 (M+).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched slowly with H2O (90 ml)
  3. extractionThe resulting aqueous phase was extracted with CH2Cl2 (2×100 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-cacb51f4a0fe486ea06a040c37bce835
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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