Sulfuric Acid → 4-Octyloxy-3-bromobenzoic acid

HRID 27644Notes

Reaction equation

HRID 27644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:5](Cl)=[O:6].[OH:20]S(O)(=O)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:5]([OH:20])=[O:6]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 198470013-Bromo-4 octyloxybenzoic acid chloride

Product 1

HCID 233334474-Octyloxy-3-bromobenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

540 mg (≃0.002 mole) of ##STR17## C5H11 and 700 mg (≃0.002 mole) of 3-bromo-4 octyloxybenzoic acid chloride are charged in a reactor containing 10 ml of pyridine and kept at ambient temperature for 48 hours. The reaction mixture is then poured into a solution containing 10 ml of concentrated H2SO4 and 100 g of ice. The organic fraction is extracted three times with ether then washed three times with water and finally dried on anhydrous Na2SO4. The solvent is evaporated and the product is recrystallised three times in ethanol. 850 ml of product are obtained. The molar efficiency is 73%. Step (d) of substituting the cyanide group for the bromine group

Workup

  1. additionThe reaction mixture is then poured into a solution
  2. extractionThe organic fraction is extracted three times with ether
  3. washthen washed three times with water
  4. dry with materialfinally dried on anhydrous Na2SO4
  5. customThe solvent is evaporated
  6. customthe product is recrystallised three times in ethanol

Sources & evidence

ORD record
ord-0817aa66841f4e4ea1624ceb904cd90c
Source dataset
uspto-grants-1980_09
Patent number
US04222888

Reaction notes

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