Thionyl Chloride → HCID 178444550, compound

HRID 2351258Notes

Reaction equation

HRID 2351258 reaction equation
C([C@H]1CC[C@H](C(Cl)=O)C1)CCCC.C(C1CC(=O)CCC1)CCCC.[CH2:26]([CH:31]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32]1)[CH2:27][CH2:28][CH2:29][CH3:30].S(Cl)(Cl)=O.[CH2:45]([C@H:48]1[CH2:53][CH2:52][C@H:51]([C:54]2[CH:59]=CC(O)=[CH:56][CH:55]=2)[CH2:50][CH2:49]1)[CH2:46][CH3:47]>CCOCC.C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:26]([C@H:31]1[CH2:35][CH2:34][C@H:33]([C:36]([O:38][C:39]2[CH:56]=[CH:55][C:54]([C@H:51]3[CH2:50][CH2:49][C@H:48]([CH2:45][CH2:46][CH3:47])[CH2:53][CH2:52]3)=[CH:59][CH:40]=2)=[O:37])[CH2:32]1)[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

9

Reactant 5

HCID 24386Thionyl ChlorideHCID 242463ethyl 3-pentylcyclopentanecarboxylateHCID 131838873-Pentylcyclohexan-1-oneHCID 86743430HCID 86743430, compoundHCID 178447901HCID 178447901, compound

Product 1

HCID 178444550HCID 178444550, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

4.0 g of trans-3-n-pentylcyclopentanecarbonyl chloride (obtainable from 5-n-pentylcyclohexanone through chlorination, Faworski rearrangement of the α-chloroketone using sodium alcoholate in ether, hydrolysis of the ethyl 3-n-pentylcyclopentanecarboxylate, alkaline isomerization of the acid and subsequent reaction with thionyl chloride) are added dropwise at 100° to a solution of 4.4 g of 4-(trans-4-n-propylcyclohexyl)-phenol and 1.6 g of pyridine in 10 ml of toluene. The mixture is allowed to react for a further 3 hours, the pyridine hydrochloride is filtered off under suction, the filtrate is washed with water and dried, and the solvent is evaporated. The residue is crystallized from ethanol. 4-(trans-4-propylcyclohexyl)-phenyl trans-3-pentylcyclopentanecarboxylate is obtained; smectic B/isotropic phase transition: 49°.

Workup

  1. customto react for a further 3 hours
  2. filtrationthe pyridine hydrochloride is filtered off under suction
  3. washthe filtrate is washed with water
  4. customdried
  5. customthe solvent is evaporated
  6. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-6fc0bf298f704e149b32480576230238
Source dataset
uspto-grants-1989_10
Patent number
US04873019

Reaction notes

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