Succinic anhydride → 4-[3,5-Dimethyl-4-methoxyphenyl)butanol

HRID 893000Notes

Reaction equation

HRID 893000 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[C:11]1(=O)O[C:14](=[O:15])[CH2:13][CH2:12]1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)(O)[O-].[Na+].O(O)O>C1(C)C=CC=CC=1.C1COCC1.C(Cl)Cl.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10]

Participants

10

Reactant 5

HCID 7922Succinic anhydrideHCID 660882,6-DimethylanisoleHCID 166717TrioxidaneHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 198945574-[3,5-Dimethyl-4-methoxyphenyl)butanol

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,6-dimethylanisole (4.45 g), succinic anhydride (4.80 g) and aluminum chloride (4.70 g) in toluene (60 ml) is stirred for 2.7 hr at 20°-25°. A 100 ml aliquot of methylene chloride is added for solubility. The reaction is run for 6 hr. The reaction is poured onto ice and extracted with methylene chloride-isopropanol. The organic phase is washed with saline, dried over sodium sulfate, concentrated and dried under reduced pressure overnight to give a solid. This material is stirred with borane-methyl sulfide complex (1.0M, 38 ml) in THF at 20°-25° for 24 hr. Aqueous sodium bicarbonate, methylene chloride and water are added. The ketoalcohol product is combined with other partly reduced materials and treated with borane-methyl sulfide complex in excess in methylene chloride for 72 hr. It is important that the ketoacid Friedel Crafts adduct should be reduced exhaustively with excess borane-methyl sulfide complex.

Workup

  1. waitThe reaction is run for 6 hr
  2. additionThe reaction is poured onto ice
  3. extractionextracted with methylene chloride-isopropanol
  4. washThe organic phase is washed with saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customdried under reduced pressure overnight
  8. customto give a solid

Sources & evidence

ORD record
ord-abfdd24c4b4246029c96adebb93b13c9
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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