Benzene → HCID 178460459, compound

HRID 1289404Notes

Reaction equation

HRID 1289404 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][OH:45])[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][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=2[F:38])[CH2:27][CH2:26]1)=[O:10].C(N(CC)CC)C.[CH:53]1[CH:58]=[CH:57]C=CC=1.[OH2:59].[C:60](Cl)(=[O:63])[CH:61]=[CH2:62]>>[C:60]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][C:53](=[O:59])[CH:58]=[CH2:57])[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][C@H:25]1[CH2:26][CH2:27][C@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=2[F:38])[CH2:29][CH2:30]1)=[O:10])(=[O:63])[CH:61]=[CH2:62]

Participants

6

Reactant 5

HCID 241Benzene2×HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178525421HCID 178525421, compound

Product 1

HCID 178460459HCID 178460459, compoundYield 33%

Procedure

First, 2.8 g of 13-[trans-4-(2,3-difluorophenyl)cyclohexyl]tridecyl 2,2-bis(6-hydroxyhexyl)acetate, 1 g of triethylamine, and 30 ml of benzene were placed in a 100 ml flask. A small amount of benzene in which 0.9 g of acryloyl chloride was dissolved was added dropwise to the reaction mixture under ice water cooling. The 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. The solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/toluene=1/20) to obtain 1.12 g of 13-[trans-4-(2,3-difluorophenyl)cyclohexyl]tridecyl 2,2-bis(6-acryloyloxyhexyl)acetate (Y: 33%). The compound thus obtained was liquid at room temperature. The compound had a purity of 99.6% by HPLC and of 1 spot by TLC.

Workup

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

Sources & evidence

ORD record
ord-4d37b84f2d514af59b428c4d93ff8cb3
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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