Resorcinol → 4-(3-Hydroxyphenoxy)benzocyclobutene

HRID 274948Notes

Reaction equation

HRID 274948 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CC(N(C)C)=O.C(=O)([O-])[O-].[K+].[K+].Br[C:22]1[CH:29]=[CH:28][CH:27]=[C:24]2[CH2:25][CH2:26][C:23]=12>C1(C)C=CC=CC=1>[OH:2][C:1]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[O:5][C:22]1[CH:29]=[CH:28][CH:27]=[C:24]2[CH2:25][CH2:26][C:23]=12

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 117898682-Bromobicyclo[4.2.0]octa-1,3,5-triene

Product 1

HCID 1317188614-(3-Hydroxyphenoxy)benzocyclobutene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Resorcinol (176.2 g, 1.60 moles), dimethylacetamide (DMAC) (550 mL), toluene (75 mL), potassium carbonate (55.2 g, 0.40 moles), 4-bromobenzocyclobutene (73.2 g, 0.40 moles), and cuprous chloride (3.96 g, 0.040 moles) are placed in a 1000 mL 3-necked flask. The flask is equipped with a water separating trap, reflux condenser, nitrogen inlet, and thermometer. The system is purged with nitrogen. The mixture is then heated to reflux, and water and toluene are collected in the trap. Toluene (about 25 mL) is distilled out of the reaction mixture and removed from the trap, until the temperature in the flask reaches 153° C. A sample, removed from the reaction after 5 hours of reflux and analyzed by gas chromatography (GC), shows little bromobenzocyclobutene remaining. The reaction is allowed to cool to room temperature after 6 hours of reflux. During the reaction, the temperature in the flask rises slightly to 156° C. by the end of the reaction.

Workup

  1. customThe flask is equipped with a water separating trap
  2. temperaturereflux condenser, nitrogen inlet
  3. customThe system is purged with nitrogen
  4. temperatureThe mixture is then heated
  5. temperatureto reflux
  6. customwater and toluene are collected in the trap
  7. distillationToluene (about 25 mL) is distilled out of the reaction mixture
  8. customremoved from the trap, until the temperature in the flask
  9. customreaches 153° C
  10. customA sample, removed from the reaction after 5 hours
  11. temperatureof reflux
  12. temperatureof reflux
  13. customDuring the reaction
  14. customthe temperature in the flask rises slightly to 156° C. by the end of the reaction

Sources & evidence

ORD record
ord-db26b8ad7b364887905aa87cdb8929b5
Source dataset
uspto-grants-1995_02
Patent number
US05391650

Reaction notes

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