2-Ethylhexanoic Acid → Sodium 2-ethylhexanoate

HRID 1851873Notes

Reaction equation

HRID 1851873 reaction equation
[OH-].[Na+:2].[CH2:3]([CH:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:6]([OH:8])=[O:7])[CH3:4]>CO>[CH2:3]([CH:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:6]([O-:8])=[O:7])[CH3:4].[Na+:2]

Participants

4

Reactant 2

HCID 86972-Ethylhexanoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 23672331Sodium 2-ethylhexanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
185 °C

Procedure

A round bottom flask (250 mL) was charged with a stir bar, sodium hydroxide (13.87 g, 0.347 mol) and methanol (200 mL) under ambient conditions. 2-Ethylhexanoic acid (50.00 g, 0.347 mol) was added dropwise to the stirred solution over 30 min. The solvent was then removed by rotary evaporation producing a white, tacky solid. This white solid was then heated at 185° C. and a pressure less that 25 torr for 18 hr, yielding anhydrous sodium 2-ethylhexanoate as a hard, white solid (97% isolated yield). Anhydrous sodium 2-ethylhexanoate is very hygroscopic and was handled under an inert and substantiallydry atmosphere.

Workup

  1. additionA round bottom flask (250 mL) was charged with a stir bar
  2. customThe solvent was then removed by rotary evaporation
  3. customproducing a white, tacky solid

Sources & evidence

ORD record
ord-70b3b559d94e42f2a96dc89597cad2ad
Source dataset
uspto-grants-2015_02
Patent number
US08957235B2

Reaction notes

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