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

HRID 2424173Notes

Reaction equation

HRID 2424173 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-41e9e6aca92d48cda10fde34ef0d4e9b
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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