4-Fluorophenol → HCID 178444513, compound

HRID 2209377Notes

Reaction equation

HRID 2209377 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-6f71b525b8734f8dab364415db3d396f
Source dataset
uspto-grants-1995_10
Patent number
US05454974

Reaction notes

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