Water → HCID 178460514, 화합물

HRID 726512

반응식

HRID 726512 반응식
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]1C[CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O>C(Cl)(=O)C=C.C1C=CC=CC=1>[C:15]([O:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)(=[O:14])[CH:16]=[CH2:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178521548HCID 178521548, 화합물

생성물 1

HCID 178460514HCID 178460514, 화합물수율 55.1%

시약·촉매·용매 2

HCID 241Benzene용매HCID 13140Acryloyl chloride용매

실험 절차

First, 2.5 g of trans-4-phenylcyclohexanol, 50 ml of tetrahydrofuran, and 1.8 g of triethylamine were placed in a 100 ml flask. A solution in which 1.7 g of acryloyl chloride was dissolved in 5 ml of benzene was added dropwise to the mixture under ice water cooling. The mixture was allowed to warm to room temperature and stirred for 5 hours. Water was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) and recrystallized from acetone to obtain 1.8 g of trans-4-phenylcyclohexyl acrylate (Y: 55.1%). The compound thus obtained had a purity of 99.7% by GC and 1 spot by TLC. Furthermore, the compound had an m.p. of 67.3° C.

후처리

  1. additionwas added dropwise to the mixture under ice water cooling
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)
  7. customrecrystallized from acetone

출처 및 근거

ORD 기록
ord-2f59842550574b84b178087ad9bd6712
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05709911

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