Water → 3-Allyl-2',6'-dichloro-biphenyl-2-ol

HRID 902301Notes

Reaction equation

HRID 902301 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18])C=C.O.CN1C[CH2:24][CH2:23][C:22]1=O>>[CH2:24]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([C:11]2[C:12]([Cl:18])=[CH:13][CH:14]=[CH:15][C:16]=2[Cl:17])[C:5]=1[OH:4])[CH:23]=[CH2:22]

Participants

4

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 691169382-Allyloxy-2',6'-dichloro-biphenyl

Product 1

HCID 689666213-Allyl-2',6'-dichloro-biphenyl-2-olYield 83%

Procedure

A solution of 2′-(allyloxy)-2,6-dichloro-1,1′-biphenyl (5.7 g, 0.0204 mol) in anhydrous 1-methyl-2-pyrrolidinone (50 mL) was heated to 180° C. for 42 hours then at 190° C. for 5 days. The cooled reaction mixture was poured into water (300 mL), the mixture stirred vigorously for 15 minutes then the resulting oily suspension extracted with ethyl acetate (400 mL). The organic extract was washed with water (300 mL) and saturated brine (300 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford a brown oil. Purification by flash chromatography using a solvent gradient of 2 to 4% ethyl acetate in hexane gave 4.71 g (83%) of 3-allyl-2′,6′-dichloro-1,1′-biphenyl-2-ol as a colorless oil. MS (ES) m/z 278.9 ([M+H]+).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe resulting oily suspension extracted with ethyl acetate (400 mL)
  3. extractionThe organic extract
  4. washwas washed with water (300 mL) and saturated brine (300 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford a brown oil
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1d47576a8cc74787a29ceca6e49b75cc
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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