Tetrahydrofuran → HCID 11959804, compound

HRID 1866823Notes

Reaction equation

HRID 1866823 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]1COC[CH2:12]1.C([Mg]Cl)=C.[Cl-].[NH4+]>O>[OH:5][CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:2]=1[OH:1])[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5227773-MethylsalicylaldehydeHCID 178461836HCID 178461836, compound

Product 1

HCID 11959804HCID 11959804, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 1 L four-necked round-bottomed flask was equipped with a magnetic stirrer bar, a thermometer and a pressure-equalizing dropping funnel. A 2-hydroxy-3-methylbenzaldehyde (30.0 g, 0.22 mol) and THF (300 ml) were added to it under a nitrogen atmosphere. After the mixture was cooled to 0° C., a solution of vinyl magnesium chloride in THF (1.9 M, 237 ml, 0.45 mol) was added thereto over 45 minutes while maintaining the mixture temperature of 15° C. or less. The mixture was gradually warmed to room temperature and stirred at room temperature for 18 hours. The mixture was cooled to 0° C. and a 20% aqueous ammonium chloride solution (600 ml) was added thereto at 0° C. After the mixture was stirred at room temperature for 30 minutes, the mixture was poured into water (500 ml). The mixture was extracted with ethyl acetate (3×500 ml). The organic layer was combined and successively washed with a 20% aqueous ammonium chloride solution (300 ml), water (2×300 ml) and a saturated aqueous NaCl solution (300 ml), followed by drying with anhydrous sodium sulfate (150 g). The solid was removed by filtration and the filtrate was concentrated to obtain 34.3 g of 2-(1-hydroxy-2-propenyl)-6-methylphenol as a brown gum.

Workup

  1. customA 1 L four-necked round-bottomed flask was equipped with a magnetic stirrer bar
  2. temperatureover 45 minutes while maintaining the mixture temperature of 15° C. or less
  3. temperatureThe mixture was gradually warmed to room temperature
  4. temperatureThe mixture was cooled to 0° C.
  5. customat 0° C
  6. stirringAfter the mixture was stirred at room temperature for 30 minutes
  7. extractionThe mixture was extracted with ethyl acetate (3×500 ml)
  8. washsuccessively washed with a 20% aqueous ammonium chloride solution (300 ml), water (2×300 ml)
  9. dry with materialby drying with anhydrous sodium sulfate (150 g)
  10. customThe solid was removed by filtration
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b12a2e6639214d32a2fd7c3232171203
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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