Acrylic Acid → 16-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-acryloyloxyhexyl)acetate

HRID 1289396Notes

Reaction equation

HRID 1289396 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][OH:49])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[F:42])=[CH:31][CH:30]=1)=[O:10].C1(P([C:63]2[CH:68]=[CH:67]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:69](O)(=[O:72])[CH:70]=[CH2:71].N(C(OCC)=O)=NC([O-])=[O:77]>O1CCCC1>[C:69]([O:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:67](=[O:77])[CH:68]=[CH2:63])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[F:42])=[CH:33][CH:34]=1)=[O:10])(=[O:72])[CH:70]=[CH2:71]

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 11776TriphenylphosphineHCID 1892087316-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-hydroxyhexyl)acetateHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 1892084816-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-acryloyloxyhexyl)acetateYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

First, 3.4 g of 16-[2,3-difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-hydroxyhexyl)acetate, 3 g of triphenylphosphine, 0.9 g of acrylic acid, and 30 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 10 ml of a solution in which 2 g of ethyl azodicarboxylate was dissolved in tetrahydrofuran was added dropwise to the mixture under ice water cooling. The resultant mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was concentrated. Thereafter, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/toluene=1/20) and recrystallized from hexane to obtain 2.7 g of 16-[2,3-difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-acryloyloxyhexyl)acetate (Y: 59.7%). The compound thus obtained had a purity of 99% by HPLC and of 1 spot by TLC. The compound had an m.p. of 33.8° C. to 35.5° C.

Workup

  1. additionwas added dropwise to the mixture under ice water cooling
  2. concentrationThe reaction mixture was concentrated
  3. customThereafter, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/toluene=1/20)
  4. customrecrystallized from hexane

Sources & evidence

ORD record
ord-4d15a69869384d4d8f3d83410bbca0cc
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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