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1,2-Dichloroethane → Phenol, 4,4'-cyclohexylidenebis[2-methyl-

HRID 35434
Notes
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Reaction equation

HRID 35434 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl[Si](C)(C)[CH3:18].[CH2:21](S)[CH2:22][CH2:23][CH3:24].Cl[CH2:27][CH2:28]Cl>C(Cl)Cl.C1CCCCC1>[CH3:8][C:1]1[CH:2]=[C:3]([C:21]2([C:12]3[CH:13]=[CH:14][C:9]([OH:15])=[C:10]([CH3:18])[CH:11]=3)[CH2:28][CH2:27][CH2:24][CH2:23][CH2:22]2)[CH:4]=[CH:5][C:6]=1[OH:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 335O-Cresol2×HCID 6397ChlorotrimethylsilaneHCID 7967CyclohexanoneHCID 8012Butanethiol

Product 1

HCID 75386Phenol, 4,4'-cyclohexylidenebis[2-methyl-Yield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

The preparation of the above cyclohexane was accomplished by repeating the procedure of Example I with the exception that o-cresol was employed in place of phenol. In addition, the preparation was affected in a 250-milliliter 3-necked round-bottomed flask with 0.2 mole of cyclohexanone, and without 1,2-dichloroethane as a solvent. Additionally, 108 grams of o-cresol, 22 grams of chlorotrimethyl silane, and 0.1 gram of butanethiol were employed. The reaction mixture was worked up by filtering it hot after the reaction, followed by slurrying up the filter cake in methylene chloride, filtering and washing several times with methylene chloride. There was obtained the cyclohexane product in a 76 percent yield after drying in vacuo at 80° C. for 12 hours, which product had a melting point of 190° to 191° C.

Workup

  1. filtrationby filtering it
  2. customhot after the reaction
  3. filtrationfiltering
  4. washwashing several times with methylene chloride
  5. customThere was obtained the cyclohexane product in a 76 percent yield
  6. customafter drying in vacuo at 80° C. for 12 hours

Sources & evidence

ORD record
ord-67f58ef83fb54c28be9b4493e5d1da62
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766255

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes