Thionyl Chloride → HCID 20186261, compound

HRID 1285030Notes

Reaction equation

HRID 1285030 reaction equation
O=S(Cl)[Cl:3].O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:25])[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1>N1C=CC=CC=1.C1C=CC=CC=1>[Cl:3][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:25])[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20186268HCID 20186268, compound

Product 1

HCID 20186261HCID 20186261, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

Next, 0.82 g of Li[AlH4 ] was added to 50 ml of dried (C2H5)2O, and the resulting mixture was stirred. Thereto was gradually added 5 g of 4-[p-(2-hydroxycarbonylethyl)phenyl]pentylcyclohexane. Thereafter the thus obtained mixture was stirred for 5 hours, and filtered. The (C2H5)2O was distilled off from the filtrate, and the residue was recrystallized from n--C6H14 to obtain 4-[p-(3-hydroxypropyl)phenyl]pentylcyclohexane. The melting point of this compound was 70.7° to 72.5° C. To a mixture of 3.6 g of SOCl2, one drop of pyridine and 50 ml of benzene was added 4.3 g of the 4-[p-(3-hydroxypropyl)phenyl]pentylcyclohexane obtained above, and the resulting mixture was refluxed for 5 hours. Thereafter, the surplus SOCl2 was distilled off to obtain 4-[p-(3-chloropropyl)phenyl]pentylcyclohexane. The melting point of this compound was 70.7° to 72.5° C.

Workup

  1. customwas 70.7° to 72.5° C
  2. customobtained above, and the resulting mixture
  3. temperaturewas refluxed for 5 hours
  4. distillationThereafter, the surplus SOCl2 was distilled off

Sources & evidence

ORD record
ord-4baccc49d80149f78e82b1f7a513b883
Source dataset
uspto-grants-1986_01
Patent number
US04564694

Reaction notes

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