Ethyl Acetate → 2-Allyloxy-5-methoxybenzyl alcohol

HRID 501728Notes

Reaction equation

HRID 501728 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:6]=1[C:7](OC)=[O:8])[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:6]=1[CH2:7][OH:8])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59560455Methyl 2-allyloxy-5-methoxybenzoate

Product 1

HCID 432678902-Allyloxy-5-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

Step AS (2). To a solution of methyl 2-allyloxy-5-methoxybenzoate (12 g, 55 mmol) in 100 mL anhydrous THF was added slowly 55 mL of a 1.0 M solution of lithium aluminum hydride (55 mmol) in THF at −50° C. The resulting solution was stirred at −50° C. for 1.5 h. EtOAc (100 mL) was added, followed by addition of 30 mL of aqueous ammonium chloride. The organic layer was filtered, washed with aqueous ammonium chloride and brine, then dried over magnesium sulfate. After concentration, 2-allyloxy-5-methoxybenzyl alcohol was obtained as a colorless oil (10.5 g, 100%), which was used directly for the next reaction without purification. LC-MS (M+H)+=195; 1H NMR (400 MHz, CDCl3) δ ppm 3.75 (s, 3H) 4.46-4.55 (m, 2H) 4.66 (s, 2H) 5.21-5.29 (m, 1H) 5.34-5.42 (m, 1H) 5.95-6.09 (m, 1H) 6.74 (dd, J=9.05, 3.02 Hz, 1H) 6.78 (d, J=9.05 Hz, 1H) 6.88 (d, J=3.02 Hz, 1H).

Workup

  1. filtrationThe organic layer was filtered
  2. washwashed with aqueous ammonium chloride and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-7ec1e836989f4b1c832633e70132d2ae
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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