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

HRID 25103Notes

Reaction equation

HRID 25103 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) δ1.62 (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-b9310816448e4f6aa42fcac0d02ae522
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Reaction notes

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