Hydrochloric Acid → Magnolol

HRID 1468254Notes

Reaction equation

HRID 1468254 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:12]2[C:13]([O:21]C)=[CH:14][CH:15]=[C:16]([CH2:18][CH:19]=[CH2:20])[CH:17]=2)[C:7]([O:10]C)=[CH:8][CH:9]=1)[CH:2]=[CH2:3].[Cl-].[Al+3].[Cl-].[Cl-].NC(N)=S.Cl>ClCCCl>[CH2:3]=[CH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:12]2[CH:17]=[C:16]([CH2:18][CH:19]=[CH2:20])[CH:15]=[CH:14][C:13]=2[OH:21])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 6451240Aluminum(III) ChlorideHCID 148642182,2'-Dimethoxy-5,5'-di(prop-2-en-1-yl)-1,1'-biphenyl

Product 1

HCID 72300Magnolol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The 4,4′-diallyl-2,2′-bianisole is added to a mixture of aluminum chloride, thiourea and 1,2-dichloroethane slowly over 3 hours at 50° C. Temperature and stirring is maintained for an additional 3-4 hours. Reaction mix is cooled and added to HCl and phases are separated. The organic layer is added to charcoal, filtered and the solvent distilled, to obtain the title compound.

Workup

  1. temperatureis maintained for an additional 3-4 hours
  2. customReaction
  3. additionmix
  4. temperatureis cooled
  5. customare separated
  6. additionThe organic layer is added to charcoal
  7. filtrationfiltered
  8. distillationthe solvent distilled

Sources & evidence

ORD record
ord-f2509bedd2584364805c2990c05f6bf6
Source dataset
uspto-grants-2015_04
Patent number
US09000231B2

Reaction notes

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