Hydrochloric Acid → HCID 11673358, compound

HRID 2102996Notes

Reaction equation

HRID 2102996 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1([S:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([CH3:18])[C:11]=2[CH3:19])[CH2:8][CH2:7][CH2:6]1.O.Cl>[OH-].[Na+].CO>[OH:17][C:13]1[C:14]([CH3:16])=[C:15]2[C:10](=[C:11]([CH3:19])[C:12]=1[CH3:18])[S:9][C:5]1([CH2:6][CH2:7][CH2:8]1)[CH2:4][C:3]2=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86605474HCID 86605474, compound

Product 1

HCID 11673358HCID 11673358, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

[1-(4-Hydroxy-2,3,5-trimethyl-phenylsulfanyl)-cyclobutyl]-acetic acid methyl ester (1.16 g) was suspended in 50 mL of 1N NaOH in MeOH and water (1:1, v/v), and the mixture was allowed to stir for 1 hour. The mixture was then acidified with 1 N HCl and extracted 3 times with ethyl acetate. The organic layer was washed with water and dried over anhydrous MgSO4, and concentrated in vacuo. The resulting acid was dissolved in 50 mL of concentrated sulfuric acid to form a homogeneous dark red solution. After 1 hour at room temperature the solution was poured into crushed ice. The resulting green mixture was extracted 3 times with ethyl acetate. The organic layer was washed with water and dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluted with 10% ethyl acetate in hexane to give 0.9 g of 6′-hydroxy-5′,7′,8′-trimethylspiro[cyclobutane-1,2′-thiochromen]-4′(3′H)-one as a yellow solid.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting acid was dissolved in 50 mL of concentrated sulfuric acid
  6. customto form a homogeneous dark red solution
  7. additionAfter 1 hour at room temperature the solution was poured
  8. custominto crushed ice
  9. extractionThe resulting green mixture was extracted 3 times with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materialdried over anhydrous MgSO4
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash chromatography
  14. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bd250a04cf554fb79e9e8b8b0837d395
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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