Hydrochloric Acid → HCID 20386043, compound

HRID 26606Notes

Reaction equation

HRID 26606 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-fb680c9925d74b0b8902f4fd2385194e
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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