Water → 4-(6-Methyloctyloxy)benzoic acid

HRID 986097Notes

Reaction equation

HRID 986097 reaction equation
[OH-:1].[Na+].[OH2:3].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12].[CH2:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18].CCO[CH2:23][CH3:24]>C(O)C>[CH3:13][CH:10]([CH2:11][CH3:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:19][C:14]1[CH:24]=[CH:23][C:17]([C:18]([OH:3])=[O:1])=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 62761-PentanolHCID 14798Sodium HydroxideHCID 135481051-Bromo-6-methyloctane

Product 1

HCID 134634574-(6-Methyloctyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50-ml three-neck flask was charged with 2.01 g of sodium hydroxide, 10 ml of water and 20 ml of ethanol, and 3.16 g of 4-n-hydroxybenzoic acid was dissolved in the charge. 4.75 g of optically active 1-bromo-6-methyloctane synthesized from commercially available amyl alcohol was added to the mixture, and reaction was carried out for 19 hours under heat and reflux. After completion of the reaction, ether washing was conducted, and the aqueous layer was recovered by filtration and made acidic. The precipitated crystals were recovered by filtration and purified to obtain 4.75 g of 4-(6-methyloctyloxy)benzoic acid.

Workup

  1. dissolutionwas dissolved in the charge
  2. additionwas added to the mixture, and reaction
  3. temperatureunder heat
  4. temperaturereflux
  5. filtrationthe aqueous layer was recovered by filtration
  6. filtrationThe precipitated crystals were recovered by filtration
  7. custompurified

Sources & evidence

ORD record
ord-9b060e2aaec645799eb9b3743018e24f
Source dataset
uspto-grants-1987_12
Patent number
US04710585

Reaction notes

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