Hydrochloric Acid → HCID 57571707, compound

HRID 2097476Notes

Reaction equation

HRID 2097476 reaction equation
O1CCOCC1.[CH:7]1([CH2:10][O:11][C:12]2[C:17]([O:18]COC)=[CH:16][CH:15]=[CH:14][C:13]=2[I:22])[CH2:9][CH2:8]1.Cl>O>[CH:7]1([CH2:10][O:11][C:12]2[C:13]([I:22])=[CH:14][CH:15]=[CH:16][C:17]=2[OH:18])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 57571706HCID 57571706, compound

Product 1

HCID 57571707HCID 57571707, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of 1,4-dioxane solution containing 33.9 g (0.10 mol) of 2-cyclopropylmethoxy-1-iodo-3-methoxymethoxybenzene obtained in Reference example 12-(b) was added 150 ml of 1,4-dioxane solution containing 4N hydrogen chloride, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, 100 ml of water was added to the reaction mixture, and the resulting mixture was extracted with diethyl ether. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 22.3 g of the title compound as a colorless oil. (Yield: 77%)

Workup

  1. customobtained in Reference example 12-(b)
  2. additionwas added to the reaction mixture
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. customThe organic layer after separation
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-48500203cbc24b529899fb54b12e2312
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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