Hydrochloric Acid → HCID 23116198, compound

HRID 495194Notes

Reaction equation

HRID 495194 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[CH2:22])[CH:16]=[C:15]([O:23][CH2:24][CH:25]=[CH2:26])[C:14]=1[CH2:27][CH3:28].Cl.C(=O)([O-])O.[Na+].O>CO.O1CCOCC1>[CH2:24]([O:23][C:15]1[C:14]([CH2:27][CH3:28])=[C:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][OH:7])[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[CH2:22])[CH:16]=1)[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 23116193HCID 23116193, compound

Product 1

HCID 23116198HCID 23116198, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(Tetrahydro-2H-pyran-2-yloxy)-1-[2-(3,5-diallyloxy-2-ethylphenyl)ethoxy]ethane (3.0 g, 7.6 mmol) obtained in Example 59, Step 1 was dissolved in methanol (30 mL), and a 4 mol/L solution of hydrogen chloride in 1,4-dioxane (20 mL) was added thereto, followed by stirring for 30 minutes. After the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, water was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane 1/9-1/1) to obtain 2-[2-(3,5-diallyloxy-2-ethylphenyl)ethoxy]ethanol (1.9 g, 81%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane 1/9-1/1)

Sources & evidence

ORD record
ord-f6f3d736eaf140788cb7566e57de09bf
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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