Hydrochloric Acid → Methyl 3-(2-formyl-3-hydroxyphenoxy)methylbenzoate

HRID 647919Notes

Reaction equation

HRID 647919 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][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[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][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462737Magnesium diiodideHCID 20484350Methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate

Product 1

HCID 22027563Methyl 3-(2-formyl-3-hydroxyphenoxy)methylbenzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate (3 g, 0.01 M) in dry tetrahydrofuran (30 ml) was added dropwise a solution of magnesium iodide (4.13 g, 0.015 M) in dry ether (65 ml). The mixture was then stirred under reflux (51/2 hr). The cooled mixture was poured into 10% hydrochloric acid (55 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solutions were washed with sodium bicarbonate solution, water, dried (magnesium sulphate) and evaporated. The residue was dissolved in chloroform-methanol (95:5) and filtered through a short pad of florisil. The pale yellow solution was evaporated to give methyl 3-(2-formyl-3-hydroxyphenoxy)methylbenzoate, m.p. 118°-120° C. from ethyl acetate/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 sodium bicarbonate solution, water
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. dissolutionThe residue was dissolved in chloroform-methanol (95:5)
  8. filtrationfiltered through a short pad of florisil
  9. customThe pale yellow solution was evaporated

Sources & evidence

ORD record
ord-58ef61e193b947428dda6d78e2b37596
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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