Acrylic Acid → HCID 178460466, compound

HRID 2392596Notes

Reaction equation

HRID 2392596 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][OH:48])=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.[C:49](O)(=[O:52])[CH:50]=[CH2:51]>ClCCl.CN(C)C1C=CN=CC=1>[C:49]([O:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([C:32]2[CH:33]=[CH:34][C:29]([C@H:26]3[CH2:25][CH2:24][C@H:23]([CH2:22][CH2:21][CH:17]4[O:18][CH2:19][CH2:20][O:16]4)[CH2:28][CH2:27]3)=[CH:30][CH:31]=2)=[CH:36][CH:37]=1)(=[O:52])[CH:50]=[CH2:51]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 178520611HCID 178520611, compound

Product 1

HCID 178460466HCID 178460466, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.38 g of dicyclohexylcarbodiimide in 5 ml of dichloromethane was added dropwise while stirring at 0°-5° C. within 5 minutes to a solution of 6.2 g of 6-[4'-[trans-4-(2-[1,3]dioxolan-2-yl ethyl)cyclohexyl]-biphenyl-4-yloxy]-hexan-1-ol, 1.48 g of acrylic acid and 1.67 g of 4-dimethylamino-pyridine in 50 ml of dichloromethane. The reaction mixture was stirred overnight, filtered and then concentrated. Chromatography of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) gave 5.14 g of 6-[4'-[trans-4-(2-[1,3]dioxolan-2-yl-ethyl)-cyclohexyl]-biphenyl-4-yloxy]-hexyl acrylate.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-faf6716ff6f4427dae0317b642567198
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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