Allyl bromide → 1,2-Dimethyl 3-(2-propen-1-yloxy)-1,2-benzenedicarboxylate

HRID 1105808Notes

Reaction equation

HRID 1105808 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[OH:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]=1[C:22]([O:24][CH3:25])=[O:23]>C(C(C)=O)C>[CH2:7]([O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]=1[C:22]([O:24][CH3:25])=[O:23])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 129015101,2-Dimethyl 3-(2-propen-1-yloxy)-1,2-benzenedicarboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The starting material can be prepared as follows: 225 g of potassium carbonate and 98 g of allyl bromide are added to a solution of 170.0 g of dimethyl 3-hydroxy-phthalate in 400 ml of methyl ethyl ketone. The mixture is heated to the reflux temperature for 18 hours, whilst stirring, and then filtered, the filter residue is washed with methyl ethyl ketone and the filtrate, combined with the wash liquid, is evaporated under reduced pressure. The residual oily crude product is distilled under reduced pressure; dimethyl 3-allyloxyphthalate is obtained as the main fraction; boiling point 126°-130°/0.015 mm Hg.

Workup

  1. customThe starting material can be prepared
  2. temperatureThe mixture is heated to the reflux temperature for 18 hours
  3. filtrationfiltered
  4. washthe filter residue is washed with methyl ethyl ketone
  5. customis evaporated under reduced pressure
  6. distillationThe residual oily crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-248dd994012b4d4baafc5018ba769a77
Source dataset
uspto-grants-1982_01
Patent number
US04310527

Reaction notes

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