4-tert-Butylphenol → 1-tert-Butyl-4-(3-chloropropoxy)benzene

HRID 1165957Notes

Reaction equation

HRID 1165957 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CC(C)=O>[CH3:3][C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:19][CH2:20][CH2:21][Cl:22])=[CH:9][CH:10]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 129286251-tert-Butyl-4-(3-chloropropoxy)benzeneYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-tert-butylphenol (20.0 g, 0.16 mol) in acetone (500 mL) were added potassium carbonate (100 g, 0.72 mol) and 1-bromo-3-chloropropane (50.6 g, 0.33 mol). The reaction was heated to 50° C. for 18 hours. The reaction was filtered and the solvents evaporated to provide 30.3 g of 3-[4-(1,1-dimethylethyl)phenoxy]-1-chloropropane as a colorless oil; 200 MHz NMR δ 1.47 (s,9H), 2.36 (p, J=5.5Hz, 2H), 3.88 (t, J=5.5 Hz, 2H), 4.22 (t, J=5.5Hz, 2H), 7.0, 7.47 (ABq, J=9.6Hz, 4H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvents evaporated

Sources & evidence

ORD record
ord-ca7eb48cf35444cda407904aa670eba8
Source dataset
uspto-grants-1990_03
Patent number
US04912222

Reaction notes

Loading…