4-Fluorophenol → HCID 178444513, compound

HRID 2050438Notes

Reaction equation

HRID 2050438 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[F:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:19][C:18]([C@H:15]2[CH2:14][CH2:13][C@H:12]([C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:7][CH2:8]3)[CH2:17][CH2:16]2)=[O:20])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 10868DicyclohexylcarbodiimideHCID 178444514HCID 178444514, compound

Product 1

HCID 178444513HCID 178444513, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 996 mg of trans-4-[trans-4-(4-pentenyl)cyclohexyl]cyclohexanecarboxylic acid in 80 ml of methylene chloride was treated with 752 mg of p-fluorophenol, 61 mg of 4-(dimethylamino)pyridine and 1.03 g of dicyclohexylcarbodiimide and stirred at room temperature for 15 hours. The reaction mixture was subsequently filtered. The filtrate was evaporated and the residue obtained was purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 3:97). Crystallization of the product obtained (1.24 g) from 40 ml of hexane gave 757 mg of pure trans-4-[trans-4-(4-pentenyl)cyclohexyl]cyclohexanecarboxylic acid 4-fluorophenyl ester with m.p. (C-N) 70.3° C. and cl.p. (N-I) 158.7° C.

Workup

  1. filtrationThe reaction mixture was subsequently filtered
  2. customThe filtrate was evaporated
  3. customthe residue obtained
  4. customwas purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 3:97)
  5. customCrystallization of the product
  6. customobtained (1.24 g) from 40 ml of hexane

Sources & evidence

ORD record
ord-ef77f7daec0243a7b5527458ee43c0c3
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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