Hydrochloric Acid → 7-(2-Formyl-3-hydroxyphenoxy)heptanoic acid

HRID 485152Notes

Reaction equation

HRID 485152 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][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[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][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462737Magnesium diiodideHCID 20271544Ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate

Product 1

HCID 130920957-(2-Formyl-3-hydroxyphenoxy)heptanoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate (4.15 g, 0.0135 M) in dry tetrahydrofuran (60 ml) was added dropwise a solution of magnesium iodide (5.82 g, 0.0202 M) in dry ether (97.5 ml). The mixture was then stirred under reflux (5 hr). The cooled mixture was poured into 10% hydrochloric acid (65 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solution were washed with water and evaporated to dryness. The residue, ethyl 7-(2-formyl-3-hydroxyphenoxyheptanoate, was dissolved in 2 N sodium hydroxide solution (50 ml) with stirring at room temperature (10 hr). The solution was decanted from a residue and acidified with concentrated hydrochloric acid with cooling. The precipitated solid was filtered off and washed well with water to give 7-(2-formyl-3-hydroxyphenoxy)heptanoic acid, m.p. 106°-107° C. from benzene/petrol.

Workup

  1. temperatureunder reflux (5 hr)
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. washThe combined organic solution were washed with water
  5. customevaporated to dryness
  6. dissolutionThe residue, ethyl 7-(2-formyl-3-hydroxyphenoxyheptanoate, was dissolved in 2 N sodium hydroxide solution (50 ml)
  7. stirringwith stirring at room temperature (10 hr)
  8. customThe solution was decanted from a residue
  9. temperaturewith cooling
  10. filtrationThe precipitated solid was filtered off
  11. washwashed well with water

Sources & evidence

ORD record
ord-718c2354ba8d4675b186c39e1954f334
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

Loading…