Hydrochloric Acid → 5-(Benzyloxy)pentanoic acid

HRID 1491997Notes

Reaction equation

HRID 1491997 reaction equation
[C:1]1(=[O:7])[O:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:8].[K+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C1(C)C=CC=CC=1.O>[CH2:10]([O:8][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:6])=[O:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 10953Delta-ValerolactoneHCID 14797Potassium Hydroxide

Product 1

HCID 104205755-(Benzyloxy)pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 100 g of δ-valerolactone, 50 ml of water, 350 ml of toluene, 280g of potassium hydroxide pellets and 300 ml of benzyl chloride is refluxed overnight with mechanical stirring and azeotroping the water with the use of a Dean-Stark apparatus. The thick white mass is cooled to room temperature and dissolved in 1 l of cold water. The organic layer is separated and the aqueous layer is condensed to 1/3 by heating over a period of 5 h. The mixture is cooled to room temperature, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×300 ml). The combined extracts are washed with brine, dried (MgSO4) and evaporated to dryness to give 5-benzyloxypentanoic acid.

Workup

  1. temperatureis refluxed overnight
  2. customazeotroping the water with the use of a Dean-Stark apparatus
  3. dissolutiondissolved in 1 l of cold water
  4. customThe organic layer is separated
  5. customcondensed to 1/3
  6. temperatureby heating over a period of 5 h
  7. temperatureThe mixture is cooled to room temperature
  8. extractionextracted with ethyl acetate (2×300 ml)
  9. washThe combined extracts are washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-a086acf2691c4023a1d7da04ebebcff4
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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