HCID 53926403, compound → HCID 67915363, compound

HRID 1608413Notes

Reaction equation

HRID 1608413 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH:5]1[CH2:10][CH:9]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C:7]([CH3:20])([CH3:19])[O:6]1>[OH-].[Na+].CO>[CH3:19][C:7]1([CH3:20])[O:6][C@@H:5]([CH2:4][C:3]([OH:21])=[O:2])[CH2:10][C@@H:9]([CH:11]=[CH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:8]1

Participants

4

Reactant 1

HCID 53926403HCID 53926403, compound

Product 1

HCID 67915363HCID 67915363, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetic acid methyl ester (8.5 g, 29.3, mmol) in 1N NaOH (32 mL) and methanol (64 mL) was heated to reflux for 45 minutes. After evaporation under reduced pressure, the aqueous solution was washed once with diethyl ether and acidified with 1N HCl (33 mL). The precipitate was collected and recrystallized from ethyl acetate/isopropyl ether to afford 7.2 g (90%) of the title compound as a colorless solid; m.p.=153°-155° C.

Workup

  1. temperatureto reflux for 45 minutes
  2. customAfter evaporation under reduced pressure
  3. washthe aqueous solution was washed once with diethyl ether
  4. customThe precipitate was collected
  5. customrecrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-25590338d0924917ad05155d153d8e1f
Source dataset
uspto-grants-1989_09
Patent number
US04870187

Reaction notes

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