Methanol → Methyl 2-ethyl-5-hydroxyvalerate

HRID 330601Notes

Reaction equation

HRID 330601 reaction equation
[CH2:1]([CH:3]1[CH2:9][CH2:8][CH2:7][O:6]C1=O)[CH3:2].[C:10](=[O:13])([O-])[O-:11].[K+].[K+].[CH3:16]O>S(=O)(=O)(O)O>[CH2:1]([CH:3]([CH2:9][CH2:8][CH2:7][OH:6])[C:10]([O:11][CH3:16])=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 36563182H-Pyran-2-one, 3-ethyltetrahydro-

Product 1

HCID 14380639Methyl 2-ethyl-5-hydroxyvalerateYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 30.0 g (0.234 mmol) of 2-ethylvalerolactone in 150 mL of dry methanol and 0.5 mL of conc. sulfuric acid was stored under argon for 17 h at 20° C. Then 10.0 g of potassium carbonate was added and the mixture stirred for 20 min. After filtration, and concentration at 40° C. under vacuum, the residue was dissolved in 100 mL of ether. The solution was washed with 200 mL of satd. sodium carbonate, 100 mL of satd. brine, dried over MgSO4, filtered, concentrated and the residue distilled to give 32.1 g (86%) of methyl 2-ethyl-5-hydroxyvalerate, bp 58°-60° C. (0.5 mm Hg).

Workup

  1. filtrationAfter filtration, and concentration at 40° C. under vacuum
  2. dissolutionthe residue was dissolved in 100 mL of ether
  3. washThe solution was washed with 200 mL of satd
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationthe residue distilled

Sources & evidence

ORD record
ord-6d93743c28334bdfad9af24ebbcab0c9
Source dataset
uspto-grants-1990_01
Patent number
US04897477

Reaction notes

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