Water → 3-(3,5-DIMETHOXY-PHENYL)-PROPAN-1-OL

HRID 1950602Notes

Reaction equation

HRID 1950602 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][CH3:16])[CH:8]=1)C.COC1C=C(CCC(OCC)=O)C=C(OC)C=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][CH2:4][OH:3])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3346402HCID 3346402, compoundHCID 21226445Aluminium lithium hydrideHCID 23087528Ethyl 3-(3,5-dimethoxyphenyl)propanoate

Product 1

HCID 113330533-(3,5-DIMETHOXY-PHENYL)-PROPAN-1-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized from 3-(3,5-dimethoxyphenyl)acrylic acid ethyl ester according to an analogous synthetic method to Example 22, ethyl 3-(3,5-dimethoxyphenyl)propionate (38.4 g) was added dropwise to a solution of lithium aluminum hydride (12.3 g) in tetrahydrofuran (200 ml) on an ice bath, and the solution was stirred for 15 minutes at room temperature. To the reaction solution were sequentially added water (12 ml), an aqueous solution of 5N sodium hydroxide (12 ml) and water (28 ml), the suspension was filtered, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (24.3 g).

Workup

  1. filtrationan aqueous solution of 5N sodium hydroxide (12 ml) and water (28 ml), the suspension was filtered
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-daa8b802bfff447da07788d5d57b14ce
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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