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

HRID 1296453Notes

Reaction equation

HRID 1296453 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-23f79d11fda04d398c49468898eba7c3
Source dataset
uspto-grants-2007_07
Patent number
US07247636B2

Reaction notes

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