Potassium Hydroxide → HCID 178443570, compound

HRID 344803Notes

Reaction equation

HRID 344803 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[O:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:13][O:12]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[K+]>CO>[OH:4][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[O:12][CH2:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][O:16]2)=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178443571HCID 178443571, compound

Product 1

HCID 178443570HCID 178443570, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

In methanol was dissolved 5 g (0.016 mole) of trans-2-(p-methoxycarbonylphenyl)-5-heptyl-1,3-dioxane, to which 1.2 equivalents of potassium hydroxide was added, and the mixture was refluxed for 8 hours with heating. After distilling methanol under reduced pressure, 300 ml of ethyl acetate was added to the residue, and the mixture was neutralized with 10% aqueous solution of hydrochloric acid while cooling at a temperature of -10° C. Then, the organic layer was concentrated and was recrystallized from methanol to give 4.2 g of trans-2-(p-hydroxycarbonylphenyl)-5-heptyl-1,3dioxane (yield: 86%).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperaturewith heating
  3. distillationAfter distilling methanol under reduced pressure, 300 ml of ethyl acetate
  4. additionwas added to the residue
  5. concentrationThen, the organic layer was concentrated
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-37813396049340ae9ac69683a74c135e
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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