Hydrochloric Acid → 3',4',5'-Trimethoxycinnamyl alcohol

HRID 1267622

Reaction equation

HRID 1267622 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].C(Cl)(=O)OCC.[BH4-].[Na+].Cl>C1COCC1.C(N(CC)CC)C>[CH3:17][O:16][C:12]1[CH:11]=[C:5]([CH:6]=[CH:7][CH2:8][OH:9])[CH:4]=[C:3]([O:2][CH3:1])[C:13]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydride

Product 1

HCID 739243',4',5'-Trimethoxycinnamyl alcohol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

3,4,5-Trimethoxycinnamic acid (1.5 g) was dissolved in THF (100 mL), triethylamine (0.64 mL) was added to the solution under ice cooling, and ethyl chlorocarbonate (0.44 mL) was then added dropwise thereto. After stirring the resultant mixture at room temperature for 1 hour, sodium borohydride (477 mg) was added to the mixture under ice cooling. After stirring the resultant mixture at room temperature for 1 hour, diluted hydrochloric acid was added to the reaction mixture to conduct extraction with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. extractionextraction with chloroform
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b1259147d3e147f487dc04a96e5576dc
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Linked notes

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