Hydrochloric Acid → HCID 90408616, compound

HRID 2275410Notes

Reaction equation

HRID 2275410 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:14])[C:5]=1[OH:15])[CH:2]=[CH2:3].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:14])[C:5]=1[OH:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67404181HCID 67404181, compound

Product 1

HCID 90408616HCID 90408616, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of the methyl 4-allyl-3-hydroxy-2-methylbenzoate (6.5 g, 31.6 mmol) in a mixture of THF:MeOH (3:1 ratio, 80 ml) at room temperature was added 25.3 g (316 mmol) of 50 w/w % aqueous NaOH solution, and the reaction mixture was stirred at 50° C. for 4 h. LCMS showed it as a clean reaction. The reaction mixture was cooled to room temperature and the methanol was removed on a rotovapor and diluted with ethyl acetate. The crude reaction mixture was acidified with 1N HCl. Some of the product precipitated out. It was diluted with water and extracted using ethyl acetate. The organic fractions were collected, dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified using an ISCO system (80 g silica column, hexane/EtOAc gradient. The product eluted ˜30% EtOAc in hexane, and the product fractions were collected and concentrated. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=8.0 Hz, 1H), 7.03 (d, J=8.0 Hz, 1H), 6.12-5.78 (m, 1H), 5.30-5.08 (m, 2H), 3.45 (d, J=6.3 Hz, 2H), 2.54 (d, J=3.7 Hz, 3H).

Workup

  1. customas a clean reaction
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe methanol was removed on a rotovapor
  4. additiondiluted with ethyl acetate
  5. customThe crude reaction mixture
  6. customSome of the product precipitated out
  7. additionIt was diluted with water
  8. extractionextracted
  9. customThe organic fractions were collected
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was purified
  14. washThe product eluted ˜30% EtOAc in hexane
  15. customthe product fractions were collected
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-58ae25daab2f4111984de4c460145a0a
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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