Toluene → HCID 131713380, compound

HRID 1388248Notes

Reaction equation

HRID 1388248 reaction equation
C(OCCC1C=CC([C:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=3)[CH2:16][CH:15]=2)=CC=1)CCC.C1(Cl)[C:33](=[O:34])[C:32](Cl)=[C:31](Cl)[C:29](=O)C=1Cl.[C:39]1(C)C(C)=CC=CC=1.[C:47]1([CH3:53])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>>[CH2:33]([O:34][CH2:39][CH2:53][C:47]1[CH:52]=[CH:51][C:50]([C:16]2[C:17]([C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=3)=[CH:18][CH:19]=[CH:14][CH:15]=2)=[CH:49][CH:48]=1)[CH2:32][CH2:31][CH3:29]

Participants

5

Reactant 4

HCID 1140TolueneHCID 7237O-XyleneHCID 8371ChloranilHCID 20470557HCID 20470557, compound

Product 1

HCID 131713380HCID 131713380, compound

Procedure

A mixture of 1-[p-(β-butyloxyethyl)-phenyl]-4-(p-bromophenyl)-cyclohexene (XV) (55 g, 0.13 mol) obtained in Step H, chloranil (78.4 g, 0.32 mol) and xylene (624 ml) was heated and placed under reflux for 24 hours. After cooling, toluene (800 ml) was added, insoluble solid filtered off and toluene removed by concentrating the filtrate. The resulting raw crystals were recrystallized from ethyl acetate (50 ml) to obtain 4"-(β-butyloxyethyl)-4-bromoterphenyl (XV1) (29 g) having a melting point of 225.7°~227.0° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. filtrationinsoluble solid filtered off
  5. customtoluene removed
  6. concentrationby concentrating the filtrate
  7. customThe resulting raw crystals were recrystallized from ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-9bef4165fb134bdc9e8d48dc3e9c7a30
Source dataset
uspto-grants-1984_02
Patent number
US04431564

Reaction notes

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