1,4-Dibromobutane → 4-(4-Bromobutoxy)phenyl 4-allyloxybenzoate

HRID 1637300Notes

Reaction equation

HRID 1637300 reaction equation
[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 153464294-Hydroxyphenyl 4-allyloxybenzoate

Product 1

HCID 193489834-(4-Bromobutoxy)phenyl 4-allyloxybenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

162.1 g (0.6 mol) of 4-hydroxyphenyl 4-allyloxybenzoate, known from U.S. Pat. No. 5,211,877, were dissolved in 3 l of methyl ethyl ketone, and 1.32 kg (6 mol) of commercial 1,4-dibromobutane, and 414 g (3 mol) of potassium carbonate were added. The mixture was heated to 80° C. with stirring and held at this temperature for 4 h. It was subsequently cooled, the remaining potassium carbonate was filtered off and the filtrate was concentrated. After the excess dibromobutane had been stripped off, the crude product was recrystallized twice from isopropanol. 4-(4-Bromobutoxy)phenyl 4-allyloxybenzoate was obtained in a yield of 90%. The ester shows the following phase behavior: C 64, N 81-85, isotropic.

Workup

  1. temperatureIt was subsequently cooled
  2. filtrationthe remaining potassium carbonate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customthe crude product was recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-c22c61fc11c54747ab5d3c4ab6e44418
Source dataset
uspto-grants-2000_03
Patent number
US06040411

Reaction notes

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