Dichloromethane → HCID 178444302, compound

HRID 2082268Notes

Reaction equation

HRID 2082268 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21](C(C)=O)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].[CH3:27]C(C)([O-])C.[K+].Cl[CH2:34][Cl:35]>C(O)(C)(C)C>[Cl:35][C:34]#[C:27][C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C@H:15]1[CH2:14][CH2:13][C@H:12]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 3104707ST002072HCID 23665647Potassium tert-butoxide

Product 1

HCID 178444302HCID 178444302, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

312.3 g (1.5 mol) of phosphorus pentachloride are added carefully to a solution of 172.4 g (1.0 mol) of methyl 4-(4-pentylcyclohexyl)phenyl ketone in 1.4 l of dichloromethane. The mixture is refluxed for 3 days and then poured onto ice; the organic phase is separated off, and the aqueous phase is extracted once with dichloromethane. The combined organic phases are evaporated on a rotary evaporator, and the residue, together with 263.2 g (2.34 mol) of potassium t-butoxide, is dissolved in 1.4 l of t-butanol. The mixture is refluxed for 15 hours and then evaporated on a rotary evaporator. The residue obtained is chromatographed on a silica gel column using petroleum ether as eluent. The eluate is evaporated on a rotary evaporator, and the product is recrystallized from petroleum ether (crystallization at -70° C.) and from 2-propanol. C 66N 70 I, η (20° C.) 13 mm2 /sec, Δn 0.208, Δε +6.7.

Workup

  1. temperatureThe mixture is refluxed for 3 days
  2. additionpoured onto ice
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted once with dichloromethane
  5. customThe combined organic phases are evaporated on a rotary evaporator
  6. temperatureThe mixture is refluxed for 15 hours
  7. customevaporated on a rotary evaporator
  8. customThe residue obtained
  9. customis chromatographed on a silica gel column
  10. customThe eluate is evaporated on a rotary evaporator
  11. customthe product is recrystallized from petroleum ether (crystallization at -70° C.) and from 2-propanol
  12. customC 66N 70 I, η (20° C.) 13 mm2 /sec, Δn 0.208

Sources & evidence

ORD record
ord-17a4d48b5f8b4cdfbec7fc7ab04dd95b
Source dataset
uspto-grants-1993_02
Patent number
US05188759

Reaction notes

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