1-Dodecanol → HCID 20363224, compound

HRID 1679080Notes

Reaction equation

HRID 1679080 reaction equation
[S:1]([C:5]1[C:6]([O:8][C:9](=[O:11])[CH:10]=1)=[O:7])([OH:4])(=[O:3])=[O:2].[CH2:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-:25].[Na+:26]>O>[CH2:12]([O:24][CH:10]([CH:5]([S:1]([OH:4])(=[O:3])=[O:2])[C:6]([O-:25])=[O:7])[C:9]([O-:8])=[O:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Na+:26].[Na+:26].[Na+:26]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 14798Sodium HydroxideHCID 124798802,5-Dioxo-2,5-dihydrofuran-3-sulfonic acid

Product 1

HCID 20363224HCID 20363224, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Sulfomaleic anhydride (10 gm) ⟦are⟧ is mixed with 80 gm (0.45 mole) of n-dodecanol and heated at 100° C for 14 hours. A solution of 7.04 gm of sodium hydroxide in 50 ml water is then added and the mixture heated at 60° C for 2 hours. The heated mixture is then extracted three times with 300 cc portions of acetone (at reflux) and the acetone insoluble fraction is then filtered, washed with additional acetone and dried to give 16.2 gm of the title compound (structure confirmed by NMR and ion exchange of a sample followed by titration with standard sodium hydroxide: neutralization equivalent: found 147.0, theory 149.3)

Workup

  1. temperaturethe mixture heated at 60° C for 2 hours
  2. extractionThe heated mixture is then extracted three times with 300 cc portions of acetone (at reflux)
  3. filtrationthe acetone insoluble fraction is then filtered
  4. washwashed with additional acetone
  5. customdried

Sources & evidence

ORD record
ord-ced978ba501e4484a877f9ef446da3b0
Source dataset
uspto-grants-1978_03
Patent number
USRE029576

Reaction notes

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