3-Chloro-1-propanol → 1-O-benzoyl-1,3-propanediol

HRID 2050026Notes

Reaction equation

HRID 2050026 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[CH2:12][CH2:13][CH2:14][OH:15]>CN(C=O)C>[C:1]([O:9][CH2:12][CH2:13][CH2:14][OH:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123133-Chloro-1-propanolHCID 517055Sodium Benzoate

Product 1

HCID 813781-O-benzoyl-1,3-propanediolYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

Sodium benzoate (96.32 g) in DMF (690 ml) was heated to 80° C., and 1-chloro-3-hydroxypropane (63.06 g) was added over 15 minutes. The temperature increased to 135° C., and the reaction mixture was heated at 135°-175° C. for 3 hours. Filtration removed 38 g of sodium chloride (97% of theory). The filtration was partially evaporated at reduced pressure at <40° C. The concentrated filtrate was poured into ice water and extracted well with ether. THe combined ether extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated. The residual oil was distilled through a Vigreux column to give 3-benzoyloxy-1-propanol (85.2 g), b.p. 124°-132° C. at 0.055 mm Hg.

Workup

  1. temperaturethe reaction mixture was heated at 135°-175° C. for 3 hours
  2. filtrationFiltration
  3. customremoved 38 g of sodium chloride (97% of theory)
  4. filtrationThe filtration
  5. customwas partially evaporated at reduced pressure at <40° C
  6. additionThe concentrated filtrate was poured into ice water
  7. extractionextracted well with ether
  8. washTHe combined ether extracts were washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. distillationThe residual oil was distilled through a Vigreux column

Sources & evidence

ORD record
ord-419a635d28014d9e9ccf0c7587d88b19
Source dataset
uspto-grants-1980_04
Patent number
US04199574

Reaction notes

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