Dimethyl Sulfoxide → 3-(2-Propenyl)-2-tetralone

HRID 1421894Notes

Reaction equation

HRID 1421894 reaction equation
[OH:1][C:2]1[CH:11]([CH2:12][CH:13]=[CH2:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1C(OC)=O.CS(C)=O.[Cl-].[Li+]>O>[CH2:12]([CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:1])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 546808303,4-Dihydro-2-hydroxy-3-(2-propenyl)-naphthalenecarboxylic Acid, Methyl Ester

Product 1

HCID 102415333-(2-Propenyl)-2-tetraloneYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

A mixture of 3,4-dihydro-2-hydroxy-3-(2-propenyl)-naphthalene carboxylic acid, methyl ester (46.1 g, crude), dimethyl sulphoxide (132 ml), water (5 ml) and lithium chloride (9.5 g, 226 mmol) was heated at 125° C., with stirring, under argon for 4.5 h. The mixture was cooled and diluted with water (750 ml) and extracted with ethyl acetate (3×1000 ml). The combined extracts were washed with water (1000 ml) and brine (1000 ml), dried (Na2SO4) and evaporated in vacuo to give a brown oil (35.5 g). This was chromatographed on silica eluting with 10% ether-hexane to give the title compound as a brown oil (25.9 g, 74%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×1000 ml)
  3. washThe combined extracts were washed with water (1000 ml) and brine (1000 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab68298f65774e77a5f9a19b670ac92c
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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