4-Methoxyphenol → Carbonic acid, methyl 2-methyl-2-propenyl ester

HRID 542578Notes

Reaction equation

HRID 542578 reaction equation
Cl[CH2:2][C:3]([CH3:5])=[CH2:4].[C:6](=[O:11])([O:9][CH3:10])[O:7][CH3:8].CO[C:14]1[CH:19]=CC(O)=C[CH:15]=1>>[C:6](=[O:9])([O:7][CH3:8])[O:11][CH2:2][C:3](=[CH2:4])[CH3:5].[CH3:5][C:3](=[CH2:4])[CH2:2][O:7][C:6](=[O:11])[O:9][CH2:10][C:14]([CH3:19])=[CH2:15]

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 112413-Chloro-2-methyl-1-propeneHCID 12021Dimethyl Carbonate

Product 2

HCID 47083Bis(2-methylprop-2-en-1-yl) carbonateYield 0.7%HCID 11029874Carbonic acid, methyl 2-methyl-2-propenyl esterYield 15.3%

Procedure

The reaction conditions of Example 37 are substantially repeated employing 3-chloro-2-methyl-l-propene (181.1 g, 2.0 moles), dimethyl carbonate (450.0 g, 5.0 moles), 30.0 g of DOWEX® MWA-1 beads and p-methoxyphenol (1.0 g, 0.08 mole). After 2 hours at 150° C., distillation gives 37.7 g (15.3 percent yield based on 3-chloro-2-methyl-1-propene) of methallyl methyl carbonate, b.p. 89° C.-90° C. (100 torr) and 1.2 g (0.7 percent yield based on 3-chloro-2-methyl-l-propene) of bis(2-methylallyl)carbonate, b.p. 87° C.-88° C. (17 torr).

Workup

  1. customThe reaction conditions of Example 37
  2. distillationdistillation

Sources & evidence

ORD record
ord-0f872ad7387046a6b8534a98aa5055bf
Source dataset
uspto-grants-1987_04
Patent number
US04658041

Reaction notes

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