Sulfuric Acid → HCID 54470623, compound

HRID 1526753Notes

Reaction equation

HRID 1526753 reaction equation
[S:1]([O-:4])([O-:3])=[O:2].[Na+].[Na+].C[O:8][C:9](=[O:26])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[OH-].[Na+].S(=O)(=O)(O)O.S(=O)=O>O.C(O)CC.O1CCCC1.CO>[S:1]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:26])=[O:8])([OH:4])(=[O:3])=[O:2]

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 1119Sulfur DioxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 2736822Methyl 16-bromohexadecanoate

Product 1

HCID 54470623HCID 54470623, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 10311-PropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27 °C

Procedure

Solutions of sodium sulfite (327 g, 2.60 mol) in water (1.26 L) and 16-bromo-hexadecanoic acid methyl ester (728 g, 2.00 mol, 96% purity) in 1-propanol (945 mL) and methanol (420 mL) were heated to reflux in 6 L reactor equipped with mechanical stirrer for 48 hours. The reaction mixture was cooled to 27° C. and diluted with tetrahydrofuran (2 L). Reaction mixture was filtered and solid material was washed with tetrahydrofuran (3×700 mL). Filtrate was cooled to 0° C. and another portion of material was precipitated. This precipitate was filtered and washed with tetrahydrofuran (2×200 mL). Solids were combined and mixed with water (8.4 L) in 20 L pot. Solution of sodium hydroxide (120 g, 3.00 mol) was added. The mixture was heated to boiling for about 5 hours. Solution of sulfuric acid (430 mL, 8.00 mol) in water (500 mL) was slowly added into the reaction mixture (sulfur dioxide is formed). Reaction mixture was heated to boiling for 10 minutes and then let to cool to 15° C. (ice bath). The mixture was filtered on Büchner funnel through filter paper Seitz (several layers filter) applying vacuo. This procedure was very slow and took two days. Solid material was several times washed with distilled water until pH of filtrate was between 2 and 3. This procedure took about three days. Muddy white material was dried in oven at 80° C. giving desired product.

Workup

  1. temperatureto reflux in 6 L reactor
  2. customequipped with mechanical stirrer for 48 hours
  3. customReaction mixture
  4. filtrationwas filtered
  5. washsolid material was washed with tetrahydrofuran (3×700 mL)
  6. temperatureFiltrate was cooled to 0° C.
  7. customanother portion of material was precipitated
  8. filtrationThis precipitate was filtered
  9. washwashed with tetrahydrofuran (2×200 mL)
  10. additionmixed with water (8.4 L) in 20 L pot
  11. temperatureThe mixture was heated
  12. customReaction mixture
  13. temperaturewas heated
  14. waitto boiling for 10 minutes
  15. temperatureto cool to 15° C. (ice bath)
  16. filtrationThe mixture was filtered on Büchner funnel
  17. filtrationthrough filter
  18. filtrationpaper Seitz (several layers filter)
  19. waittook two days
  20. washwashed with distilled water until pH of filtrate
  21. waitThis procedure took about three days
  22. customMuddy white material was dried in oven at 80° C.

Sources & evidence

ORD record
ord-c275140d5fe04618b6e799cb528795fc
Source dataset
uspto-grants-2015_07
Patent number
US09085637B2

Reaction notes

Loading…