Benzene, 1,2-dichloro-4-methyl- → HCID 12660316, 화합물

HRID 1158274

반응식

HRID 1158274 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[S].ClC1C=C(C)C=CC=1Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 7256Benzene, 1,2-dichloro-4-methyl-HCID 286707HCID 286707, 화합물HCID 5362487Sulfur

생성물 1

HCID 12660316HCID 12660316, 화합물수율 22.9%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
200 °C

실험 절차

In a 50-ml, eggplant-shaped flask equipped with a magnetic stirrer and a reflux condenser were placed 6.6 g (30 mmole) of the 2-(4-chlorobenzylidene)cyclohexanone obtained in Example 12, 1.44 g (45 mmole) of sulfur and 12 ml of 3,4-dichlorotoluene in this order. The system was made vacuum using an aspirator and then returned to ordinary pressure using nitrogen; and this operation was repeated three times. The system was stirred for 4 hours at a bath temperature of 200° C. and then cooled to room temperature. 50 ml of toluene was added to the system, followed by extraction with 50 ml of a 10% aqueous sodium hydroxide solution; and this operation was repeated twice. The aqueous layer was washed with 50 ml of toluene. Then, 35% hydrochloric acid was added to the aqueous layer until the aqueous layer became acidic, followed by extraction with 50 ml of ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then subjected to vacuum distillation to remove ethyl acetate, to obtain 1.5 g of a brown oil. The oil was subjected to Kugel Rohr distillation to obtain 0.6 g of light yellow crystals. Yield: 9% The purity of the intended product in the crystal was 97.8% as measured by high performance liquid chromatography.

후처리

  1. customIn a 50-ml, eggplant-shaped flask equipped with a magnetic stirrer and a reflux condenser
  2. temperaturecooled to room temperature
  3. extractionfollowed by extraction with 50 ml of a 10% aqueous sodium hydroxide solution
  4. washThe aqueous layer was washed with 50 ml of toluene
  5. additionThen, 35% hydrochloric acid was added to the aqueous layer until the aqueous layer
  6. extractionfollowed by extraction with 50 ml of ethyl acetate
  7. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationsubjected to vacuum distillation
  10. customto remove ethyl acetate

출처 및 근거

ORD 기록
ord-023b2175bec54301af75c3421b633df4
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807856B2

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