N,N-Dimethylaniline → 3-allyl-biphenyl-4-ol

HRID 2120612Notes

Reaction equation

HRID 2120612 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)C=C.CN(C)[C:19]1[CH:24]=CC=C[CH:20]=1>C(OCC)C>[CH2:24]([C:10]1[CH:9]=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]=1[OH:4])[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 2579864-[(Prop-2-en-1-yl)oxy]-1,1'-biphenyl

Product 1

HCID 2584593-allyl-biphenyl-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-allyloxy-biphenyl 65 (5.03 g, 23.9 mmol) in 20 ml of dimethylaniline was heated at 170° C. for 5 hr. The mixture was diluted with 250 ml diethyl ether and washed with 1M HCl solution. The ether phase was washed with brine, dried and concentrated to give a brown solid. The crude product was recrystallized from cyclohexane to give 2.69 g 3-allyl-biphenyl-4-ol 66. The mother liquor was concentrated and chromatographed (7% ethyl acetate/hexane) to give an additional 2.13 g of 2-allyl-4-phenyl-phenol 66.

Workup

  1. washwashed with 1M HCl solution
  2. washThe ether phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a brown solid
  6. customThe crude product was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-3de4f3539bf744b9ab907bf413ff0c94
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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