Dicyclohexylcarbodiimide → HCID 178442095, compound

HRID 1198327

Reaction equation

HRID 1198327 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([F:34])[C:28]=2[F:35])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19][CH3:20].[CH2:36]([C@H:41]1[CH2:46][CH2:45][C@H:44]([C:47](O)=[O:48])[CH2:43][CH2:42]1)[CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)Cl>[CH2:36]([C@H:41]1[CH2:42][CH2:43][C@H:44]([C:47]([O:33][C:30]2[CH:31]=[CH:32][C:27]([C:24]3[CH:23]=[CH:22][C:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=3)=[C:28]([F:35])[C:29]=2[F:34])=[O:48])[CH2:45][CH2:46]1)[CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 191036434'-Pentyl-2,3-difluorobiphenyl-4-olHCID 178444557HCID 178444557, compound

Product 1

HCID 178442095HCID 178442095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.1 mol of dicyclohexylcarbodiimide (DCC) dissolved in CH2Cl2 is added to 0.1 mol of 4'-pentyl-2,3-difluorobiphenyl-4-ol (which can be prepared from 4'-pentyl-2,3-difluoro-4-methoxy-biphenyl by ether cleavage with HBr/glacial acetic acid), 0.1 mol of trans-4-n-pentyl-cyclohexanecarboxylic acid and a catalytic amount of 4-N,N'-dimethylaminopyridine (DMAP) in 300 ml of CH2Cl2 at 0° C., with exclusion of moisture. The mixture is then stirred at room temperature for 12 hours, the dicyclohexylurea which has precipitated is separated off and the product is worked up in the customary manner. The product is purified by crystallization. 4'-Pentyl-2,3-difluorobiphenyl-4-yl trans-4-n-Pentylcyclohexanecarboxylate is obtained, C 44° N 159.1° I.

Workup

  1. customat 0° C.
  2. customthe dicyclohexylurea which has precipitated
  3. customis separated off
  4. customThe product is purified by crystallization

Sources & evidence

ORD record
ord-408bf51ab9bb414cb99c8b65607d7ea1
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Linked notes

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