2-Propenoic acid, 3-(3-methoxyphenyl)- → m-Methoxycinnamyl alcohol

HRID 1007139Notes

Reaction equation

HRID 1007139 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH:12]=[CH:13][C:14](O)=[O:15].[K+].[Br-]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH:12]=[CH:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-HCID 253877Potassium BromideHCID 21226445Aluminium lithium hydride

Product 1

HCID 53401715m-Methoxycinnamyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (213 mg; 5.5 mmol) was added portionwise to anhydrous THF (10 ml) at 0° C. To this a solution of 3-methoxycinnamic acid (2 g; 11 mmol) in THF (5 ml) was added. The reaction was left to stir at 0° C. for 10 min and then allowed to reach ambient temperature. The reaction mixture was quenched with 2M aqueous sodium hydroxide (15 ml) and the aqueous layer was extracted with ether (3×15 ml). The combined organic layers were washed with 2M hydrochloric acid (3×15 ml), brine (3×15 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel, and the product was isolated as an oil (222 mg: 12%). IR (cm−1; KBr): (3400, OH) (1400; C═C) (1250; OCH3); 1H-NMR CDCl3: (3.8, s; 3H) (4.3, dd; 2H) (6.3, m; 1H) (6.6, d; 1H) (6.8, dd; 1H) (6.9, t; 1H) (7.0, d; 1H) (7.2, t: 1H); 13C-NMR CDCl3: 55.3, 63.6, 111.9, 113.4, 119.2, 128.9, 129.6, 131.0, 138.2, 158.2, 159.9; Mass Spectrum (M+) m/e: 164.

Workup

  1. waitThe reaction was left
  2. customto reach ambient temperature
  3. customThe reaction mixture was quenched with 2M aqueous sodium hydroxide (15 ml)
  4. extractionthe aqueous layer was extracted with ether (3×15 ml)
  5. washThe combined organic layers were washed with 2M hydrochloric acid (3×15 ml), brine (3×15 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. customthe product was isolated as an oil (222 mg: 12%)

Sources & evidence

ORD record
ord-88f0a62be65e4c31bd9264a2f197b13c
Source dataset
uspto-grants-2004_09
Patent number
US06794384B1

Reaction notes

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