Dicyclohexylcarbodiimide → HCID 178444291, compound

HRID 370368Notes

Reaction equation

HRID 370368 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:25]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1)[CH2:26][CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:20]([C@H:17]1[CH2:18][CH2:19][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][C:34]([C@H:31]4[CH2:32][CH2:33][C@H:28]([CH2:25][CH2:26][CH3:27])[CH2:29][CH2:30]4)=[O:35])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 178444287HCID 178444287, compoundHCID 178448101HCID 178448101, compound

Product 1

HCID 178444291HCID 178444291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.40 g of 4-hydroxy-4'-(trans-4-pentylcyclohexyl)biphenyl, 0.21 g of trans-4-propylcyclohexanecarboxylic acid and 0.025 g of (4-dimethylamino)pyridine were dissolved in 25 ml of dichloromethane and then 0.31 g of N,N'-dicyclohexylcarbodiimide was added portionwise within 10 minutes while stirring. The mixture was left to stand at room temperature for 3 days and then the precipitate was filtered off. The filtrate was diluted with dichloromethane, washed twice with 20 ml of saturated sodium bicarbonate solution each time and then with water, dried over sodium sulphate and concentrated. The crude trans-4-propylcyclohexanecarboxylic acid 4'-(trans-4-pentylcyclohexyl)-4-biphenylyl ester obtained was chromatographed on silica gel with hexane/dioxane (volume ratio 19:1). The fractions which were pure according to thin-layer chromatography were pooled and recrystallized from ethyl acetate. Yield 0.33 g; m.p. (C-S) 92° C., cl.p. (N-I) 319° C.; further phase transitions: S-S 154° C., S-S 218.5° C., S-N 240° C.

Workup

  1. waitThe mixture was left
  2. filtrationthe precipitate was filtered off
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed twice with 20 ml of saturated sodium bicarbonate solution each time
  5. dry with materialwith water, dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41d3b56709164df594885a18414facfe
Source dataset
uspto-grants-1985_07
Patent number
US04526704

Reaction notes

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