Hydrochloric Acid → 2-Cyclopropyl-6-methylphenyl acetate

HRID 1866836Notes

Reaction equation

HRID 1866836 reaction equation
[Mg].C1COCC1.[C:7]([O:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH:18](Br)[CH2:19][CH2:20]Br)(=[O:9])[CH3:8].Cl>C1(C)C=CC=CC=1.O>[C:7]([O:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH:18]1[CH2:20][CH2:19]1)(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 5462224MagnesiumHCID 119598052-(1,3-Dibromopropyl)-6-methylphenyl acetate

Product 1

HCID 119598072-Cyclopropyl-6-methylphenyl acetateYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
75 °C

Procedure

A 300 ml four-necked round-bottomed flask was equipped with a magnetic stirrer bar, a thermometer, a reflux condenser and a drying tube. Magnesium (1.50 g, 61.7 mmol), toluene (15 ml) and anhydrous THF (15 ml) were added to the flask under a nitrogen atmosphere. The mixture was heated in an oil bath of 75° C. for 15 minutes (temperature of the mixture was 62-64° C.). Subsequently, the mixture was heated in an oil bath of 75° C. and a solution of 2-(1,3-dibromopropyl)-6-methylphenyl acetate (17.9 g, purity: 67%, 34.3 mmol) in toluene (60 ml) was added thereto over 30 minutes. The temperature of the mixture was raised to 89° C. After the mixture was stirred in an oil bath of 75° C. for 5.5 hours, the mixture was cooled and 6M hydrochloric acid (20.5 ml, 123 mmol) was added dropwise thereto over 15 minutes such that the temperature of the reaction mixture did not exceed 45° C. After the mixture was stirred at room temperature for 1 hour, it was diluted with water (20 ml) and it was stirred for 10 minutes. The solution was separated and the organic layer was successively washed with a saturated aqueous NaHCO3 solution (50 ml) and water (50 ml) and concentrated to obtain 11.1 g (purity: 45.2%, 26.4 mmol) of 2-cyclopropyl-6-methylphenyl acetate as a brown gum.

Workup

  1. customA 300 ml four-necked round-bottomed flask was equipped with a magnetic stirrer bar
  2. customwas 62-64° C.
  3. temperatureSubsequently, the mixture was heated in an oil bath of 75° C.
  4. temperatureThe temperature of the mixture was raised to 89° C
  5. temperaturethe mixture was cooled
  6. waitover 15 minutes such that the temperature of the reaction mixture did not exceed 45° C
  7. stirringAfter the mixture was stirred at room temperature for 1 hour
  8. stirringwas stirred for 10 minutes
  9. customThe solution was separated
  10. washthe organic layer was successively washed with a saturated aqueous NaHCO3 solution (50 ml) and water (50 ml)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-8336c6a500ed46ffbc85ef1e79146c76
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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