Hydrochloric Acid → HCID 22999255, compound

HRID 1166797Notes

Reaction equation

HRID 1166797 reaction equation
CC1(C)CO[CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]([OH:23])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:10][CH:9]=2)[O:4]C1.O.Cl>C1COCC1.C([O-])(O)=O.[Na+]>[OH:23][CH:18]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH:5]=[O:4])=[CH:9][CH:10]=1)[CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22999159HCID 22999159, compound

Product 1

HCID 22999255HCID 22999255, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-[4-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-naphthyl]-3-methyl-1-butanol (1.76 g, 5.35 mmol) in THF (10 mL) was added water (1 mL) and conc. HCl (1 mL). The solution was stirred at room temp. for 16 hours, diluted with NaHCO3-solution (20 mL), and extracted with ether (3×30 mL). The combined organic extracts were dried and concentrated. Flash chromatography (silicagel, hexanes:ethyl acetate, 4:1) provided 900 mg (70%) colorless oil.

Workup

  1. extractionextracted with ether (3×30 mL)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ae3ae22d3841a580e44846f7c033d9
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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