Sodium Hydroxide → HCID 11401443, compound

HRID 2103124Notes

Reaction equation

HRID 2103124 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[C:4]([O:10]C)[CH:3]=1.[Br:12]Br.[OH-].[Na+]>C(Cl)(Cl)Cl.ClCCl.C(Cl)(Cl)(Cl)Cl>[Br:12][C:7]1[CH:6]=[C:5]([OH:8])[C:4](=[CH:3][C:2]=1[CH3:1])[OH:10]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 681263,4-Dimethoxytoluene

Product 1

HCID 11401443HCID 11401443, compound

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of homoveratrole (136.4 g, 1.1 mol) in chloroform (1.2 L) and dichloromethane (300 mL) was slowly added a solution of bromine (66 mL, 1.28 mol, 1.2 eq.) in carbon tetrachloride (250 mL). After 5 hours the reaction mixture was neutralized to pH7 with an aqueous solution of sodium hydroxide and the aqueous layer was extracted with chloroform. The combined organic layer was dried over sodium sulfate, filtered, and the volatiles were removed in vacuo, affording the title compound as a light brown solid, m.p.: 92-98° C.

Workup

  1. extractionthe aqueous layer was extracted with chloroform
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-903978a768114c3eba85badad5b0dde0
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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