Allyl bromide → HCID 118689797, compound

HRID 2209319Notes

Reaction equation

HRID 2209319 reaction equation
[CH3:1][C:2]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:22](=O)([O-])[O-].[K+].[K+].[CH3:28][C:29](N(C)C)=O.[CH2:34](Br)[CH:35]=[CH2:36].[CH3:38][CH2:39][CH2:40]CCC>O.C1(C)C=CC=CC=1>[CH2:34]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:22][CH:29]=[CH2:28])=[CH:10][CH:9]=2)([CH3:1])[CH2:3][CH2:4][C:5]([O:7][CH2:40][CH:39]=[CH2:38])=[O:6])=[CH:16][CH:17]=1)[CH:35]=[CH2:36]

Participants

8

Reactant 5

HCID 7841Allyl bromide2×HCID 8058HexaneHCID 11430Potassium Carbonate2×HCID 31374Dimethylacetamide2×HCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Product 1

HCID 118689797HCID 118689797, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A 5-L flask equipped with a stirrer, thermometer, and nitrogen purging line was charged with 458 g of diphenolic acid, 884 g of potassium carbonate, and 2,000 g of dimethylacetamide. With stirring in a nitrogen atmosphere at room temperature, 774 g of allyl bromide was added dropwise, followed by stirring at 60° C. for 58 hours. With the temperature kept, 221 g of potassium carbonate, 193 g of allyl bromide and 500 g of dimethylacetamide were added, followed by stirring at 60° C. for 20 hours. Under ice cooling, 2,000 g of water was added dropwise to quench the reaction. Then 1,000 g of toluene, 1,000 g of hexane, and 2,000 g of water were added to the reaction solution, from which an organic layer was taken out. The organic layer was sequentially washed with 2,000 g of water, four 500-g portions of water, and 500 g of saturated saline solution. Thereafter the solvent was distilled off, obtaining 686 g of allyl 4,4-bis(4-allyloxyphenyl)pentanoate in crude form.

Workup

  1. customA 5-L flask equipped with a stirrer
  2. stirringby stirring at 60° C. for 58 hours
  3. stirringby stirring at 60° C. for 20 hours
  4. customto quench
  5. customthe reaction
  6. washThe organic layer was sequentially washed with 2,000 g of water, four 500-g portions of water, and 500 g of saturated saline solution
  7. distillationThereafter the solvent was distilled off

Sources & evidence

ORD record
ord-a9ec3c1bb20346cbbe5ee61126dc9e48
Source dataset
uspto-grants-2016_06
Patent number
US09377689B2

Reaction notes

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