Hydrochloric Acid → HCID 20386043, compound

HRID 46973Notes

Reaction equation

HRID 46973 reaction equation
O1CCCCC1O[CH:8]([CH2:10][CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH3:9].CO.Cl.C(OCC)(=[O:26])C>O>[C:18]([O:17][CH:11]([CH2:12][O:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:8][CH2:9][OH:26])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 867363612-Tetrahydropyranyloxy-4-acetoxy-5-propoxypentane

Product 1

HCID 20386043HCID 20386043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-tetrahydropyranyloxy-4-acetoxy-5-propoxypentane (11.5 g., 0.42 mole), methanol (700 ml.), concentrated hydrochloric acid (3 ml.) and ethyl acetate (70 ml.) is stirred at room temperature for 1 hour. The reaction mixture is poured into cold H2O (1500 ml.) and the organic layer is extracted with ether. The combined extracts are washed with saturated sodium bicarbonate solution, then brine, and dried over anhydrous magnesium sulfate. The solvent is removed under vacuum and the residual oil is distilled to give the title compound as a light yellow oil.

Workup

  1. extractionthe organic layer is extracted with ether
  2. washThe combined extracts are washed with saturated sodium bicarbonate solution
  3. dry with materialbrine, and dried over anhydrous magnesium sulfate
  4. customThe solvent is removed under vacuum
  5. distillationthe residual oil is distilled

Sources & evidence

ORD record
ord-e03a6ba0f6e64c1c8447ec4bd476e7b9
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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