Ethanol → ethyl 4,4-diethoxypentanoate

HRID 1952853Notes

Reaction equation

HRID 1952853 reaction equation
[O:1]=[C:2]([CH3:10])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(OCC)(OCC)[O:12][CH2:13][CH3:14].[CH2:21](O)[CH3:22]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:21]([O:1][C:2]([O:12][CH2:13][CH3:14])([CH3:10])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 10883Ethyl levulinateHCID 31214Ethyl orthoformate

Product 1

HCID 523027ethyl 4,4-diethoxypentanoateYield 72.5%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 171.3 g (1.19 mol) of ethyl 4-oxopentanoate, 207 ml (184.2 g, 1.24 mol) of triethyl orthoformate, 26 ml of absolute ethanol and 1 g of p-toluenesulfonic acid was refluxed for 8 h with vigorous stirring and then distilled under reduced pressure. 187.9 g (72.5%) of ethyl 4,4-diethoxypentanoate were obtained, boiling point 104-106° C./14 mm Hg.

Workup

  1. temperaturewas refluxed for 8 h
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-64bd6f0af8974541a784a1c7f5d0b1e0
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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