Hydrochloric Acid → Ethyl 5-(2-formyl-3-hydroxyphenoxy)pentanoate

HRID 647910Notes

Reaction equation

HRID 647910 reaction equation
[CH:1]([C:3]1[C:18]([O:19]C)=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:2].[I-].[Mg+2].[I-].Cl>O1CCCC1.CCOCC>[CH:1]([C:3]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462737Magnesium diiodideHCID 20484342Ethyl 5-(2-formyl-3-methoxyphenoxy)pentanoate

Product 1

HCID 9838209Ethyl 5-(2-formyl-3-hydroxyphenoxy)pentanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 5-(2-formyl-3-methoxyphenoxy)pentanoate (Example 4) (4.38 g, 0.0156 M) in dry tetrahydrofuran (45 ml) was added dropwise a solution of magnesium iodide (6.533 g, 0.0235 M) in dry ether (95 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 solutions were washed with water, dried (sodium sulphate) and evaporated. The oily residue was chromatographed on silica gel eluting with chloroform to give ethyl 5-(2-formyl-3-hydroxyphenoxy)pentanoate, m.p. 32°-33° C.

Workup

  1. temperatureunder reflux (5 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. customThe oily residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-6826ba84def9491d8cfd444614bd8515
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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