Hydrochloric Acid → 2-(4,4-Dimethyl-chroman-7-yl)-heptanoic acid

HRID 899298Notes

Reaction equation

HRID 899298 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.C(#N)C.I([O-])(=O)(=O)=[O:25].[Na+].Cl>C(Cl)(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:25])=[O:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 121490662-(4,4-Dimethyl-chroman-7-yl)-heptan-1-olHCID 23667635Sodium periodate

Product 1

HCID 226406782-(4,4-Dimethyl-chroman-7-yl)-heptanoic acidYield 56.2%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.27 g, 0.98 mmole, from Example 1, step 6) in a mixture of 2 mL of carbon tetrachloride, 2 mL acetonitrile and 3 mL water, containing 3-5 mg of ruthenium chloride, was added 0.85 g of sodium periodate. The mixture was stirred at room temperature for 2 hours, diluted with 10 mL of water, and pH was adjusted to 2 with 10% hydrochloric acid. The mixture was extracted with three 10 mL portions of dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a dark oil. The product was purified by flash chromatography (SiO2, gradient from 0 to 20% ethyl acetate in hexanes) to yield 0.16 g of 2-(4,4-dimethyl-chroman-7-yl)-heptanoic acid as a pale yellow oil.

Workup

  1. extractionThe mixture was extracted with three 10 mL portions of dichloromethane
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a dark oil
  6. customThe product was purified by flash chromatography (SiO2, gradient from 0 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-265f42b3d96a4c34900cae9b09e60a87
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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