4-(3,4-Dimethoxyphenyl)butanoic acid → 4-(3,4-Dimethoxyphenyl)butan-1-ol

HRID 458604Notes

Reaction equation

HRID 458604 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 3236754-(3,4-Dimethoxyphenyl)butanoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 122205824-(3,4-Dimethoxyphenyl)butan-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(3,4-Dimethoxyphenyl)butyric acid (13 g, 58 mmol) was dissolved in dry THF (150 mL) then BH3.THF (110 mL, 1M solution, 110 mmol) was added drop wise with vigorous stirring under an argon atmosphere. The reaction mixture was then stirred overnight at room temperature. After this time, the reaction was quenched with water and 10% HCl solution at 0° C. and extracted with ethyl acetate. The organic fraction was dried with sodium sulfate and passed through a pad of silica gel. The solvent was removed at reduced pressure to give 23 (12.0 g, 99%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.62 (m, 4H), 2.0 (s, 1H), 2.62 (m, 2H), 3.65 (m, 2H), 3.82 (s, 3H), 3.84 (s, 3H) 6.67–6.82 (m, 3H).

Workup

  1. stirringThe reaction mixture was then stirred overnight at room temperature
  2. customAfter this time, the reaction was quenched with water and 10% HCl solution at 0° C.
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic fraction was dried with sodium sulfate
  5. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-35002d2c51fe46059ac9755a6728edfd
Source dataset
uspto-grants-2007_03
Patent number
US07192959B2

Reaction notes

Loading…