HCID 20186273, compound → HCID 20186268, compound

HRID 1285029Notes

Reaction equation

HRID 1285029 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:8][CH:7]=1)=O>CCOCC>[OH:1][CH2:2][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:22])[CH2:13][CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 20186273HCID 20186273, compound

Product 1

HCID 20186268HCID 20186268, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. stirringThereafter the thus obtained mixture was stirred for 5 hours
  2. filtrationfiltered
  3. distillationThe (C2H5)2O was distilled off from the filtrate
  4. customthe residue was recrystallized from n

Sources & evidence

ORD record
ord-2f8c2e1575de4542818ac9362809c7c5
Source dataset
uspto-grants-1986_01
Patent number
US04564694

Reaction notes

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