Methallyl alcohol → 2-Methyl-1,4-butanediol

HRID 372409

Reaction equation

HRID 372409 reaction equation
C[O:2][CH:3]1[CH2:7][CH:6]([CH3:8])[CH2:5][O:4]1.C(O)C(=C)C.[H][H]>[Cr]([O-])([O-])=O.[Cu+2].O>[CH3:8][CH:6]([CH2:7][CH2:3][OH:2])[CH2:5][OH:4].[CH3:8][CH:6]1[CH2:5][O:4][C:3](=[O:2])[CH2:7]1

Participants

7

Reactant 3

HCID 10557Methallyl alcoholHCID 12270516HCID 12270516, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 180532-Methyl-1,4-butanediolYield 70%HCID 98451beta-Methyl-gamma-butyrolactoneYield 4%

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 962WaterSolvent

Procedure

The process is carried out as in Examples 1 - 5 using 50.0 grams of a methanolic co-distillate (boiling range 66° - 78° C) containing 14.8 grams of 2-methoxy-4-methyltetrahydrofuran derived from methallyl alcohol as described in step (a), 30 ml of water and 5.0 grams of powdered copper chromite (Catalysts and Chemicals Co.). The mixture is heated at 180° C under 1000 psi of hydrogen for one hour. Analysis of the product mixture shows the presence of 9.3 grams of 2-methyl-1,4-butandiol (70% yield) and about 0.5 grams of 3-methyl-4-butyrolactone (4% yield).

Sources & evidence

ORD record
ord-b5220fa9d52240789ee45f8917821a5c
Source dataset
uspto-grants-1978_05
Patent number
US04091041

Linked notes

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