Water → 2,3-Difluoro-4'-[12,12-bis(acryloyloxymethyl)dodecyl]oxybiphenyl

HRID 1289380Notes

Reaction equation

HRID 1289380 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][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:30][OH:31])[CH2:28][OH:29])=[CH:11][CH:10]=1.C(N(CC)CC)C.[O:39]1[CH2:43][CH2:42][CH2:41]C1.O.[C:45](Cl)(=[O:48])[CH:46]=[CH2:47]>>[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][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:28][O:29][C:43](=[O:39])[CH:42]=[CH2:41])[CH2:30][O:31][C:45](=[O:48])[CH:46]=[CH2:47])=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 189208462,3-Difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl

Product 1

HCID 189208682,3-Difluoro-4'-[12,12-bis(acryloyloxymethyl)dodecyl]oxybiphenylYield 57%

Procedure

First, 2.4 g of 2,3-difluoro-4'-[12,12-bis(hydroxymethyl)dodecyl]oxybiphenyl, 1.3 g of triethylamine, and 100 ml of tetrahydrofuran were placed in a 200 ml flask. Then, 15 ml of tetrahydrofuran solution in which 1.1 g of acryloyl chloride was dissolved was added dropwise to the reaction mixture under ice water cooling, and the resultant reaction mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was poured into water, and an organic layer was extracted with ether. The ether layer was washed with diluted hydrochloric acid and water in this order, and then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1) and recrystallized from hexane to obtain 1.7 g of 2,3-difluoro-4'-[12,12-bis(acryloyloxymethyl)dodecyl]oxybiphenyl (Y: 57%). The compound thus obtained had a purity of 99.6% by GC, 100% by HPLC, and 1 spot by TLC. The compound thus obtained had an m.p. of 33.4° C. to 34.4° C.

Workup

  1. additionwas added dropwise to the reaction mixture under ice water cooling
  2. customthe resultant reaction mixture
  3. extractionan organic layer was extracted with ether
  4. washThe ether layer was washed with diluted hydrochloric acid and water in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled away
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1)
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-555dcde752ec4a2593cb9152ed174dc0
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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