Chlorobutanol → Methacrylic Acid

HRID 591115

Reaction equation

HRID 591115 reaction equation
[Cl:1][C:2]([Cl:8])([Cl:7])[C:3]([CH3:6])([OH:5])[CH3:4].[Cl:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12]>CO>[C:11]([O:13][CH3:14])(=[O:12])[C:10]([CH3:16])=[CH2:15].[C:11]([OH:13])(=[O:12])[C:10]([CH3:16])=[CH2:15].[C:11]([O:5][C:3]([CH3:6])([CH3:4])[C:2]([Cl:8])([Cl:7])[Cl:1])(=[O:12])[C:10]([CH3:16])=[CH2:15].[Cl:9][C:10]([CH3:16])([CH3:15])[C:11]([O:5][C:3]([CH3:6])([CH3:4])[C:2]([Cl:8])([Cl:7])[Cl:1])=[O:12]

Participants

7

Reactant 2

HCID 5977ChlorobutanolHCID 211144Methyl 2-chloro-2-methylpropanoate

Product 4

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 118163057(1,1,1-Trichloro-2-methyl-2-propyl) methacrylateHCID 118163068(1,1,1-Trichloro-2-methyl-2-propyl) 2-chloro-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2.83 g of the crude reaction solution obtained was added 0.11 g of methanol, followed by heating at 60° C. for 4 hours. Then, it was found out by gas chromatography analysis that the conversion of the 1,1,1-trichloro-2-methyl-2-propanol was 86.0% and the yield of methyl 2-chloro-2-methylpropanoate was 10.2%. As to other products, it was obtained methyl methacrylate in a 0.2% yield, methacrylic acid in a 8.7% yield, (1,1,1-trichloro-2-methyl-2-propyl) methacrylate in a 13.1% yield, and (1,1,1-trichloro-2-methyl-2-propyl) 2-chloro-2-methylpropanoate in a 22.8% yield.

Workup

  1. customTo 2.83 g of the crude reaction solution
  2. customobtained

Sources & evidence

ORD record
ord-77e6c5fd78e34424b45ba1d920c490c3
Source dataset
uspto-grants-2016_01
Patent number
US09238612B2

Linked notes

Loading…