Isopropanol → HCID 178440805, compound

HRID 1460408Notes

Reaction equation

HRID 1460408 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=CC=C[CH:3]=1.[CH:9](O)([CH3:11])[CH3:10].[OH-:13].[Na+].Br[C:16]([CH3:21])([CH3:20])[C:17](O)=O>O>[CH2:17]([C:2]([CH3:7])([CH3:3])[C:1]([OH:13])=[S:8])[C:16]1[CH:21]=[CH:11][CH:9]=[CH:10][CH:20]=1

Participants

6

Reactant 4

HCID 3776Isopropanol2×HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 749242-Bromo-2-methylpropanoic acid

Product 1

HCID 178440805HCID 178440805, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Benzylmercaptan (415 ml; 3.5 mol) was added to isopropanol (800 ml), and under cooling, 5.3 N aqueous sodium hydroxide (1000 ml) and an isopropanol solution (800 ml) containing bromoisobutyric acid (1) (296 g; 1.77 mol) were dropwise added thereto. The resulting mixture was heated at 80° C. for 44 hours while stirring. The reaction mixture was combined with water (1000 ml) and washed with ether three times. The aqueous layer was adjusted to pH 2 with 4N hydrochloric acid, followed by extraction with ethyl acetate two times. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride in order three times. The organic layers were combined together, dried over anhydrous sodium sulfate and concentrated. Ether (5 liters) was added to the residue, and dicyclohexylamine (353 ml) was dropwise added thereto under cooling. Precipitated crystals were collected by filtration and recrystallized from a mixture of methanol and ether to give benzylthioisobutyric acid (dicyclohexylamine salt) (2) (348.7 g; yield, 50%).

Workup

  1. temperatureunder cooling
  2. additionwere dropwise added
  3. washwashed with ether three times
  4. extractionfollowed by extraction with ethyl acetate two times
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionEther (5 liters) was added to the residue, and dicyclohexylamine (353 ml)
  9. additionwas dropwise added
  10. temperatureunder cooling
  11. customPrecipitated crystals
  12. filtrationwere collected by filtration
  13. customrecrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-9510d2d7dded43d38aeee3b8816850e8
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

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