Benzoic Acid → 5-Hydroxypentyl benzoate

HRID 657471

Reaction equation

HRID 657471 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([O:9][CH2:10][CH2:11][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

5

Reactant 3

HCID 243Benzoic AcidHCID 6101p-Toluenesulfonic acidHCID 81051,5-Pentanediol

Product 1

HCID 5698735-Hydroxypentyl benzoateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of benzoic acid (1 g), 1,5-pentanediol (5 mL) and p-toluenesulfonic acid (110 mg) was heated in an oil-bath at 100° C. overnight. The reaction mixture was cooled to room temperature, poured into water (50 mL) and extracted with EtOAc (2×25 mL), washed with sodium carbonated (5%, 20 mL) followed by brine (15 mL). The organic layer was dried over anhyd. sodium sulfate, filtered and concentrated to give almost pure product (1.15 g, 67%);

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×25 mL)
  3. washwashed with sodium
  4. customThe organic layer was dried over anhyd
  5. filtrationsodium sulfate, filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-155d34d436e840d59a60ff2dac6381b7
Source dataset
uspto-grants-2011_12
Patent number
US08076303B2

Linked notes

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