Hydrochloric Acid → HCID 14510786, compound

HRID 2298726Notes

Reaction equation

HRID 2298726 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][CH:10]2[C:16]([O:18]C)=[O:17])=[CH:5][CH:4]=1.Cl>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@@H:10]2[C:16]([OH:18])=[O:17])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14664466HCID 14664466, compound

Product 1

HCID 14510786HCID 14510786, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolane 4-carboxylate (2.0 g, 7.5 mmol) and aqueous sodium hydroxide solution (0.36 g in 20 ml) and industrial methylated spirits (20 ml) were stirred at 80° C. for 3 hours. The mixture was cooled to room temperature, neutralised with dilute hydrochloric acid and concentrated in vacuo. The product was extracted with DCM, dried over NaSO4 and evaporated to dryness to leave (5R,4S)-5-(4-methoxyphenyl)2,2-dimethyl-1,3-dioxolane-4-carboxylic acid as a colourless oil (1.7 g, 90%). 1H-NMR was in accordance with expected signals. I.R. showed expected peaks.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe product was extracted with DCM
  3. dry with materialdried over NaSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4cbfb645f629463bb7e1b28f4a9ba2cd
Source dataset
uspto-grants-2002_12
Patent number
US06495217B2

Reaction notes

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