Hydrochloric Acid → 5-(2-Formyl-3-hydroxyphenoxy)-2,2-dimethylpentanoic acid

HRID 647917Notes

Reaction equation

HRID 647917 reaction equation
[CH:1]([C:3]1[C:20]([O:21]C)=[CH:19][CH:18]=[CH:17][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12]CC)=[O:11])=[O:2].[I-].[Mg+2].[I-].Cl>O1CCCC1.CCOCC>[CH:1]([C:3]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:15])([CH3:16])[C:10]([OH:12])=[O:11])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462737Magnesium diiodideHCID 20484344Ethyl 5-(2-formyl-3-methoxyphenoxy)-2,2-dimethylpentanoate

Product 1

HCID 99034285-(2-Formyl-3-hydroxyphenoxy)-2,2-dimethylpentanoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 5-(2-formyl-3-methoxyphenoxy)-2,2-dimethylpentanoate (6.46 g, 0.021 M) in dry tetrahydrofuran (60 ml) was added dropwise a solution of magnesium iodide (8.67 g, 0.031 M) in dry ether (130 ml). The mixture was then stirred under reflux (51/2 hr). The cooled mixture, containing ethyl 5-(2-formyl-3-hydroxyphenoxy)-2,2-dimethylpentanonate, was poured into 10% hydrochloric acid (110 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solutions were washed with water, dried (sodium sulphate) and evaporated. The residue was dissolved in 95% ethanol (50 ml) and 2 N sodium hydroxide solution (100 ml) and stirred at room temperature (20 hr). The solution was then evaporated and the residue diluted with water and extracted with ether. The aqueous phase was acidified with concentrated hydrochloric acid with cooling and the solid produced filtered off and washed with water to give 5-(2-formyl-3-hydroxyphenoxy)-2,2-dimethylpentanoic acid, m.p. 76°-77° C. from benzene/petrol.

Workup

  1. temperatureunder reflux (51/2 hr)
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. washThe combined organic solutions were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. dissolutionThe residue was dissolved in 95% ethanol (50 ml)
  8. stirring2 N sodium hydroxide solution (100 ml) and stirred at room temperature (20 hr)
  9. customThe solution was then evaporated
  10. additionthe residue diluted with water
  11. extractionextracted with ether
  12. temperaturewith cooling
  13. customthe solid produced
  14. filtrationfiltered off
  15. washwashed with water

Sources & evidence

ORD record
ord-a7a32108c97f47a8a1c69004790f904a
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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