Sulfuric Acid → Ethyl 5-ethoxyheptanoate

HRID 1789521Notes

Reaction equation

HRID 1789521 reaction equation
[OH:1][CH:2]([CH2:9][CH3:10])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11](C1OC(=O)CCC1)[CH3:12].[CH2:20](OC(OCC)OCC)[CH3:21].Cl(O)(=O)(=O)=O.[OH-].[Na+].S(=O)(=O)(O)O>C(O)C>[CH2:11]([O:1][CH:2]([CH2:9][CH3:10])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:20][CH3:21])=[O:7])[CH3:12]

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 31214Ethyl orthoformate2×HCID 102968delta-HeptalactoneHCID 5282895Delta-hydroxy enanthoic acid

Product 1

HCID 13924080Ethyl 5-ethoxyheptanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 400 g 5-hydroxyheptanoic acid and 6-ethyltetrahydro-2H-pyran-2-one (400 g) is added to the reaction vessel containing ethanol (4000 ml) and triethylorthoformate (4000 ml). Perchloric acid (160 ml) is slowly added. The mixture is stirred at room temperature for 4 hours, after which time sodium hydroxide pellets (230 g) are added to stop the reaction. Once the sulfuric acid has been neutralized the ethanol and triethylorthoformate are removed under vacuum. The residue is partitioned between ether (2000 ml) and water (1000 ml). The organic phase is separated and the aqueous layer extracted with ether (3×500 ml). The organic layers are combined and dried over anhydrous sodium sulfate. The remaining solvent is removed under vacuum leaving a clear orange oil. The crude product is fractionally distilled under reduced pressure leaving a clear, colorless oil (302 g, 1.49 moles), BP 120° C./10 cm Hg.

Workup

  1. additionis added to the reaction vessel
  2. customthe reaction
  3. customare removed under vacuum
  4. customThe residue is partitioned between ether (2000 ml) and water (1000 ml)
  5. customThe organic phase is separated
  6. extractionthe aqueous layer extracted with ether (3×500 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe remaining solvent is removed under vacuum
  9. customleaving a clear orange oil
  10. distillationThe crude product is fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-f0be817ce3d042319adc6ba51ba5d29c
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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