Acetic Acid → 2-Methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-ol

HRID 1250962Notes

Reaction equation

HRID 1250962 reaction equation
[Li].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.[CH3:18][C:19]([CH3:21])=[O:20].C(O)(=O)C>O1CCCC1>[CH3:18][C:19]([OH:20])([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1)[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 3028194LithiumHCID 226096115-(3-Bromopropyl)-1,2,3-trimethoxybenzene

Product 1

HCID 226095282-Methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-olYield 24.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To anhydrous tetrahydrofuran (10 ml) stirred in an ice bath under nitrogen were added 104 mg (15 mmol) of lithium, 3.9 g (14 mmol) of 1-bromo-3-(3,4,5-trimethoxyphenyl)propane (1), and a solution of 0.95 ml (13 mmol) of acetone in tetrahydrofuran (10 ml). After the mixture was stirred for 17 hours at room temperature, a 2% aqueous solution of acetic acid (50 ml) chilled with ice was added to conduct extraction with diethyl ether. An organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil (4.1 g) was purified by column chromatography on silica gel, thereby obtaining 860 mg (yield: 24%) of 2-methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-ol.

Workup

  1. additionwas added
  2. extractionextraction with diethyl ether
  3. washAn organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil (4.1 g) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c97ce0cd51f946e19ad2ffb01d22343c
Source dataset
uspto-grants-2002_01
Patent number
US06340682B1

Reaction notes

Loading…