Acrylic Acid → HCID 178460483, compound

HRID 2392594Notes

Reaction equation

HRID 2392594 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][CH2:17][CH2:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C@H:26]2[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]2)[CH2:22][CH2:21]1.[C:35](O)(=[O:38])[CH:36]=[CH2:37]>CN(C)C1C=CN=CC=1.ClCCl>[C:35]([O:16][CH2:17][CH2:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C@H:26]2[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]2)[CH2:22][CH2:21]1)(=[O:38])[CH:36]=[CH2:37]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 178525713HCID 178525713, compound

Product 1

HCID 178460483HCID 178460483, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4.2 g of N,N'-dicyclohexylcarbodiimide were added within 5 minutes while stirring to a solution of 5.2 g of trans-4-(trans-4-[3-hydroxypropyl]cyclohexyl)cyclohexanecarboxylic acid, 1.2 g of acrylic acid and 0.2 g 4-(dimethylamino)pyridine in 25 ml of dichloromethane. The reaction mixture was stirred overnight, filtered and then concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which were pure according to thin-layer chromatography gave 4.2 g of trans-4-(trans-4-[3-acryloyloxypropyl]cyclohexyl)cyclohexanecarboxylic acid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which

Sources & evidence

ORD record
ord-66ff2191bca149fbba9c43e295757ccb
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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