3',4'-Dimethoxycinnamic acid → 3-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

HRID 1743883

Reaction equation

HRID 1743883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].O=S(Cl)Cl.COC(=O)C=CC1C=CC(OC)=C(OC)C=1.[H-].C([Al+]CC(C)C)C(C)C>CO.C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][CH2:8][OH:9]

Participants

8

Reactant 4

HCID 168483',4'-Dimethoxycinnamic acidHCID 24386Thionyl ChlorideHCID 94307Methyl 3,4-dimethoxycinnamateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 3627113-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 0.42 g (2.0 mmol) of 3,4-dimethoxycinnamic acid in 50 ml MeOH was added SOCl2 (50 μl) and the mixture was stirred at 60° C. for 5 h. Methanol was taken to dryness and the obtained 3,4-dimethoxycinnamic acid methyl ester was reduced with 1M THF solution of diisobutylaluminum hydride (8.0 mmol) in absolute THF (50 ml) at 20° C. for 1 h. Water was added, the mixture was extracted with EtOAc, dried with MgSO4 and distilled in vacuo (Kugelrohr apparatus (Aldrich), 0.1 mm Hg, T. oven 185–190° C.) giving an off-white solid, yield 0.36 g (92%), m.p. 70–71° C. The product gave the following analytical data:

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialdried with MgSO4
  3. distillationdistilled in vacuo (Kugelrohr apparatus (Aldrich), 0.1 mm Hg, T. oven 185–190° C.)
  4. customgiving an off-white solid, yield 0.36 g (92%), m.p. 70–71° C
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-a573c8ebd94e4386890348f62d6ffa40
Source dataset
uspto-grants-2006_03
Patent number
US07012095B2

Linked notes

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