Hydrochloric Acid → 1-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-one

HRID 1161031Notes

Reaction equation

HRID 1161031 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]C(=O)N(C)C)=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2].[OH-].[K+].C(O)C.Cl>O>[OH:19][C:5]1[C:6]([CH2:16][CH2:17][CH3:18])=[C:7]([SH:10])[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 2801555S-(4-Acetyl-3-hydroxy-2-propylphenyl) dimethylcarbamothioate

Product 1

HCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a stirred mixture of dimethyl-thiocarbamic acid S-(4-acetyl-3-hydroxy-2-propyl-phenyl)ester (1.08 g, 3.84 mmol), potassium hydroxide (1.1 g, 19.2 mmol), ethanol (25 mL), and water (10 mL) for 2 hours. Cool the reaction in an ice/water bath and adjust the pH to 2 with aqueous 5N hydrochloric acid. Extract the mixture with ethyl acetate (3×50 mL). Combine the extracts and wash with water (50 mL) and brine (50 mL) and dry over magnesium sulfate, filter, and concentrate to afford the title compound (0.76 g, 94%) as a brown oil which solidifies on standing. LCMS (m/z) 211 M−1.

Workup

  1. temperatureReflux
  2. temperatureCool
  3. customthe reaction in an ice/water bath
  4. extractionExtract the mixture with ethyl acetate (3×50 mL)
  5. washCombine the extracts and wash with water (50 mL) and brine (50 mL)
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-71fadf6ad9c74936bb1982ea3affd9fc
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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