(3,5-Dimethoxyphenyl)acetic acid → 2-(3,5-Dimethoxyphenyl)ethanol

HRID 273268

Reaction equation

HRID 273268 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C:18](O)=[O:19])[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1>O1CCOCC1>[CH3:16][O:15][C:13]1[CH:12]=[C:11]([CH:10]=[C:9]([O:8][CH3:7])[CH:14]=1)[CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 138316(3,5-Dimethoxyphenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2656342-(3,5-Dimethoxyphenyl)ethanolYield 103.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of LiAlH4 (1.05 g) in dioxane (100 ml) was added a solution of 3,5-dimethoxyphenyl acetic acid (5.32 g) in dioxane (20 ml) portionwise at 0° C. The mixture was stirred at room temperature for 0.5 hour and at 50° C. for 2 hours. The mixture was quenched with conc. NH4OH and filtered through Celite. The filtrate was evaporated to yield 3,5-dimethoxyphenethyl alcohol (5.1 g). IR (Neat) 3400, 1600 cm−1; MS (GC−EI) 182 (M+), 151 (M—MeO).

Workup

  1. customThe mixture was quenched with conc. NH4OH
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-98fc9dd307094083928613de837213f1
Source dataset
uspto-grants-2008_11
Patent number
US07456217B2

Linked notes

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