1-Dodecanol → HCID 20363224, compound

HRID 1287220Notes

Reaction equation

HRID 1287220 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 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-f86eb40e126c42298a9d2af2739664da
Source dataset
uspto-grants-1976_10
Patent number
US03984408

Reaction notes

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