Acrylic Acid → HCID 18920854, compound

HRID 1289411Notes

Reaction equation

HRID 1289411 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[CH:11][CH:10]=1.[C:38]([OH:42])(=O)[CH:39]=[CH2:40].[C:43]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:48]=CC=C[CH:44]=1.N(C(OCC)=O)=NC([O-])=[O:65]>O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:38](=[O:42])[CH:39]=[CH2:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:44](=[O:65])[CH:43]=[CH2:48])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 11776TriphenylphosphineHCID 18920851HCID 18920851, compoundHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 18920854HCID 18920854, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 2.3 g of 2,3-difluoro-4'-[8,8-bis(6-hydroxyhexyl)octyl]oxybiphenyl, 0.8 g of acrylic acid, 2.9 g of triphenylphosphine, and 50 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 1.93 g of ethyl azodicarboxylate was added dropwise to the reaction mixture under ice water cooling. Thereafter, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (eluent: benzene) to obtain 1.31 g of 2,3-difluoro-4'-[8,8-bis(6-acryloyloxyhexyl)octyl]oxybiphenyl (Y: 47.1%). The compound thus obtained was liquid at room temperature. The compound had a purity of 99.5% by HPLC and 1 spot by TLC.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (eluent: benzene)

Sources & evidence

ORD record
ord-9db77c08f65f47129c12fee968133a6c
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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