3,4-Dihydroxybenzaldehyde → Dilinoleylbenzaldehyde

HRID 1367797노트

반응식

HRID 1367797 반응식
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=O.[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)(=O)C>COCCOCCOC>[CH2:5]([C:4]1[C:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:2]([CH:9]=[CH:8][CH:7]=1)[CH:11]=[O:14])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

참가 물질

5

반응물 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 59753235Linoleyl methanesulfonate

생성물 1

HCID 86608586Dilinoleylbenzaldehyde수율 98.7%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
100 °C

실험 절차

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Linoleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.9 g (94%) of a brown oil.

후처리

  1. customsealed
  2. customflushed with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe solids were washed with 1,2-dichloroethane
  6. concentrationThe combined filtrate and washes were concentrated
  7. customdried under high vacuum at 65° C.
  8. customto remove residual diglyme
  9. customThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-bc952a918b744b2898bc986ca7bcf4b9
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893302B2

반응 노트

불러오는 중…