Ethanol → Ethyl 5-benzyloxypentanoate

HRID 1491998Notes

Reaction equation

HRID 1491998 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](O)[CH3:17].S(=O)(=O)(O)O>C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 104205755-(Benzyloxy)pentanoic acid

Product 1

HCID 18953758Ethyl 5-benzyloxypentanoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 61.1 g of 5-benzyloxypentanoic acid, 566 ml of ethanol and 10 ml of concentrated sulfuric acid is refluxed for 15 h. The mixture is cooled to room temperature, 10 ml of triethylamine are added and evaporated. The residue is diluted with 250 ml of ether and the solution is washed in water and brine dried (MgSO4) and evaporated. The residual oil is distilled to give ethyl 5-benzyloxypentanoate, b.p. 110°-113° C. (0.7 mm/Hg).

Workup

  1. temperatureis refluxed for 15 h
  2. customevaporated
  3. additionThe residue is diluted with 250 ml of ether
  4. washthe solution is washed in water
  5. dry with materialbrine dried (MgSO4)
  6. customevaporated
  7. distillationThe residual oil is distilled

Sources & evidence

ORD record
ord-6690fe47460a4ce08d4c3bc3fbdb9b2d
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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