Diethyl Ether → (3,5-dimethoxy-4-propan-2-yl-phenyl)methanol

HRID 252312Notes

Reaction equation

HRID 252312 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:22][CH3:23])[C:18]=1[CH2:19][CH2:20]C)[C:12]([O:14]C)=O.[CH3:24]COCC>>[CH3:23][O:22][C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([O:8][CH3:7])[C:18]=1[CH:19]([CH3:20])[CH3:24])[CH2:12][OH:14]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 21226445Aluminium lithium hydrideHCID 66842732HCID 66842732, compound

Product 1

HCID 46928175(3,5-dimethoxy-4-propan-2-yl-phenyl)methanolYield 88%

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (95%) (5.00 g, 125 mmol) in dry ether (100 mL) at 0° C. was added a solution of methyl 3,5-dimethoxy-4-1-propylbenzoate (15.7 g, 90.1 mmol), in ether (300 mL) under N2. The suspension was stirred at 0° C. for one hour then for an additional hour at room temperature. The reaction was quenched by slow addition of a saturated Na2SO4 aqueous solution (10 mL) at 0° C. The mixture was stirred overnight. The solid was filtered off and the filtrate was evaporated to dryness to give the desired alcohol (13.8 g, 88% yield) as white crystals. 1HNMR (CDCl3. ppm): δ 1.34 (d, J=7.2 Hz, 6H), 3.65 (hept., J=7.2 Hz, 1H), 3.88 (s, 6H), 4.70 (s, 2H), 6.62 (s, 2H).

Workup

  1. waitfor an additional hour at room temperature
  2. customThe reaction was quenched by slow addition of a saturated Na2SO4 aqueous solution (10 mL) at 0° C
  3. stirringThe mixture was stirred overnight
  4. filtrationThe solid was filtered off
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-57c789fe56734750919553508243adb0
Source dataset
uspto-grants-2011_01
Patent number
US07868047B2

Reaction notes

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