HCID 53926403, compound → HCID 67915363, compound

HRID 621727Notes

Reaction equation

HRID 621727 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-8b29d0cfc9e34d84acccae3f98c04509
Source dataset
uspto-grants-1989_04
Patent number
US04824959

Reaction notes

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