Guaiacol → HCID 1622515, compound

HRID 917486Notes

Reaction equation

HRID 917486 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[C:10]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11]1.[O-]CC.[K+].C(=O)(O)[O-].[Na+]>>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH2:13][CH2:12][CH2:11][C:10]([OH:15])=[O:14]

Participants

5

Reactant 4

HCID 460GuaiacolHCID 7302Gamma-ButyrolactoneHCID 516892Sodium BicarbonateHCID 23670592Potassium ethoxide

Product 1

HCID 1622515HCID 1622515, compoundYield 55%

Conditions

Temperature
110 °C

Procedure

To the mixture of guaiacol (2-methoxyphenol, 1.0 equivalent) and γ-butyrolactone, cooled in an ice-water bath, was added potassium ethoxide in small portions. The reaction mixture was heated at 110° C. overnight, and then at 155° C. for an additional 10 hours. The mixture was then poured into ice water, basified to pH 9.5 with saturated sodium bicarbonate, and extracted with chloroform. The aqueous phase was separated, acidified to pH 2.5 with 2N HCl, and extracted with a mixture of chloroform:isopropyl alcohol (3:1). The organic phase was dried over anhydrous sodium sulfate and evaporated to afford 4-(2-methoxyphenoxy)butanoic acid as a light brown oil in 55% yield. The crude product was used for next reaction without further purification: 1H NMR δ 6.90 (m, 4H), 4.08 (t, 2H, J=6.2 Hz), 3.85 (s, 3H), 2.62 (t, 2H, J=7.2 Hz), 2.16 (p, 2H, J=6.6 Hz).

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionextracted with chloroform
  3. customThe aqueous phase was separated
  4. extractionextracted with a mixture of chloroform:isopropyl alcohol (3:1)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-fe8e723f174e485cbfb31526a2a96925
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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