Hydrochloric Acid → 1-(4-Ethoxyphenyl)-2-methylpropan-1-ol

HRID 1977723Notes

Reaction equation

HRID 1977723 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.C([Li])CCC.[CH:16](=[O:20])[CH:17]([CH3:19])[CH3:18].Cl>O1CCCC1.CCCCCC>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:16]([OH:20])[CH:17]([CH3:19])[CH3:18])=[CH:3][CH:4]=1)[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 685234-BromophenetoleHCID 178418339Butyllithium

Product 1

HCID 158254611-(4-Ethoxyphenyl)-2-methylpropan-1-olYield 100.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of p-bromophenetole (2.01 g, 0.01 mol) in tetrahydrofuran is cooled to −65° C., treated dropwise with a 2.5 M solution of n-butyllithium in hexane (4 mL), stirred for 20 minutes at −55 to −65° C., treated dropwise with a solution of isobutyraldehyde (0.91 mL, 0.01 mol) in tetrahydrofuran, stirred overnight at room temperature, diluted with an ice-water mixture, acidified with 10% hydrochloric acid, and extracted with methylene chloride. The combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a tan oil (1.95 g) which is identified by NMR spectral analyses.

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b219047515384776bd2ec2e209c5c7c3
Source dataset
uspto-grants-2001_05
Patent number
US06235754B1

Reaction notes

Loading…