Hydrochloric Acid → 2-(4,4-Dimethyl-chroman-7-yl)-heptan-1-ol

HRID 899271Notes

Reaction equation

HRID 899271 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:12](=[CH2:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[OH-:20].[Na+].OO.Cl>C1COCC1.O>[CH3:19][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][OH:20])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 226406814,4-Dimethyl-7-(1-methylene-hexyl)-chroman

Product 1

HCID 121490662-(4,4-Dimethyl-chroman-7-yl)-heptan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-dimethyl-7-(1-methylene-hexyl)-chroman (0.442 g, 1.71 mmole) in 8 mL of THF at 0° C. was treated with 1.71 mL of 1M BH3.THF complex. The reaction mixture was stirred at room temperature for three hours and then cooled to 0° C. The mixture was treated successively with 0.3 mL of water, 0.34 mL of 3M sodium hydroxide and 0.34 mL of 30% hydrogen peroxide, stirred at room temperature for two hours and then diluted with 10 mL of water. The pH was adjusted to 4.0 with 10% HCl and extracted with three 12.5 mL portions of ether. The combined-organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The product was purified by flash chromatography (SiO2, 10-20% ethyl acetate in hexanes) to yield 0.366 g of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol as a colorless oil.

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred at room temperature for two hours
  3. extractionextracted with three 12.5 mL portions of ether
  4. dry with materialThe combined-organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 10-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2ed67997a530424180f3a1203ecdcb61
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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