Sulfuric Acid → HCID 53745704, compound

HRID 2392970Notes

Reaction equation

HRID 2392970 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[OH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11].S(=O)(=O)(O)O>>[OH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[O:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74203-Hydroxybenzoic AcidHCID 123133-Chloro-1-propanol

Product 1

HCID 53745704HCID 53745704, compoundYield 108.4%

Procedure

3-Chloro-1-propanol (161.6 g, 1.71 mol) was refluxed with 3-hydroxy-benzoic acid (40.0 g, 0.29 mol) and a catalytic amount of sulfuric acid for a total of 9 hours. The excess alcohol was removed by vacuum distillation. The resulting orange oil was diluted with 400 mL of water and neutralized to pH 7. The solution was extracted with ethyl acetate (3×250 mL). The organic layer was washed with 100 mL of brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography with to give 67.5 g of product which contained a small amount of the starting alcohol: 1H NMR (CDCl3) δ2.24 (quint, 2H), 3.70 (t, 2H), 4.48 (t, 2H, J=6 Hz), 5.55 (s, 1H), 7.05-7.63 (m, 4H). ##STR21##

Workup

  1. customfor a total of 9 hours
  2. customThe excess alcohol was removed by vacuum distillation
  3. additionThe resulting orange oil was diluted with 400 mL of water and neutralized to pH 7
  4. extractionThe solution was extracted with ethyl acetate (3×250 mL)
  5. washThe organic layer was washed with 100 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was purified by column chromatography with

Sources & evidence

ORD record
ord-3edd72a3bcf5418f9ddf9efe81687eb6
Source dataset
uspto-grants-1998_09
Patent number
US05804103

Reaction notes

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