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

HRID 899295Notes

Reaction equation

HRID 899295 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.Cl.[OH2:22]>>[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:22])=[O:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 121490662-(4,4-Dimethyl-chroman-7-yl)-heptan-1-ol

Product 1

HCID 226406782-(4,4-Dimethyl-chroman-7-yl)-heptanoic acidYield 50%

Procedure

A solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.2 g, 0.72 mmol, from Example 5.1, Step 6) in 1.5 mL of CCL4 and 2.2 mL of water containing 4 mg RuCl3 was treated with 628 mg, 2.94 mmol of NaIO4. The mixture was stirred at room temperature for 2.5 h, diluted with 10 mL of water and the pH adjusted to 2 with 10% aqueous HCl. The mixture was extracted with dichloromethane, concentrated to dryness, and purified via flash chromatography (0-20% ethyl acetate/hexane gradient elution) to give 105 mg (50%) of 2-(4,4-dimethyl-chroman-7-yl)-heptanoic acid.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. concentrationconcentrated to dryness
  3. custompurified via flash chromatography (0-20% ethyl acetate/hexane gradient elution)

Sources & evidence

ORD record
ord-cf5725918df144e4bc02961a1ccd5272
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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