Methanol → Butanoic acid, 2-hydroxy-4-(methylthio)-, methyl ester

HRID 2352051Notes

Reaction equation

HRID 2352051 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O-:5])=[O:4].[Ca+2].O[CH:12](CCSC)C([O-])=O.CO.OS(O)(=O)=O>C(Cl)Cl>[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O:5][CH3:12])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1073442-Hydroxy-4-(methylthio)-butanoic acid calcium salt (2:1)

Product 1

HCID 10261421Butanoic acid, 2-hydroxy-4-(methylthio)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercial calcium 2-hydroxy-4-(methylthio)-butyrate (20 g, 0.12 mol) was suspended in 250 ml CH2Cl2. CH3OH (15 ml, 0.36 mol) was added and the mixture cooled to 10° C., at which point H2SO4 (3.7 ml, 0.07 mol) was added. An obvious physical change in the slurry was noted. The mixture was heated at reflux for 60 minutes, by which time tlc indicated reaction was nearly complete. As a matter of convenience, the reaction mixture was stirred 64 hours at room temperature, at which time insoluble byproducts were removed by filtration. The filtrate was washed with 150 ml each of saturated NaHCO3 and brine, dried (MgSO4) and stripped to yield title product as an oil; tlc Rf 0.8 (ethyl acetate)0.25 (3:1 hexane:ethyl acetate).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 60 minutes, by which time
  4. customtlc indicated reaction
  5. customwere removed by filtration
  6. washThe filtrate was washed with 150 ml each of saturated NaHCO3 and brine
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-35482625bf2a4d708317e1ca7325b5e9
Source dataset
uspto-grants-1989_10
Patent number
US04874877

Reaction notes

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