Phenol → Phenyl 3-phenylprop-2-enoate

HRID 251783

반응식

HRID 251783 반응식
C(Cl)(=O)/C=C/C1C=CC=CC=1.C1(O)C=CC=CC=1.C(N(CC)CC)C.[C:26]1([O:32][C:33](=[O:42])/[CH:34]=[CH:35]/[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.O.C1COCC1>[C:26]1([O:32][C:33](=[O:42])[CH:34]=[CH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

8

반응물 4

HCID 996PhenolHCID 8471TriethylamineHCID 785207Phenyl CinnamateHCID 5354261Cinnamoyl Chloride

생성물 1

HCID 95152Phenyl 3-phenylprop-2-enoate

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a 1-L three-neck flask, under a nitrogen gas stream, trans-cinnamic acid chloride (100 g, 0.60 mol), phenol (59.3 g, 0.63 mol), and THF (500 ml) were fed, and a THF solution (100 ml) of triethylamine (63.8 g, 0.63 mol) were added dropwise using a dripping funnel while being chilled with ice. After the completion of dropwise addition, 12-hour stirring was performed at room temperature, and the reaction solution was poured into water. The obtained white precipitate was filtered and dried under reduced pressure, and thereafter the yield was 135.5 g (yield rate of 99.9%). This was dissolved into approximately 200 ml of methanol by heating, and then cooled. As a result, white crystal was obtained (112.6 g, yield rate of 83.8%). Note that, the obtained crystal was confirmed to be a target trans-cinnamic acid phenyl ester by NMR structural analysis.

후처리

  1. temperaturewhile being chilled with ice
  2. additionAfter the completion of dropwise addition, 12-hour
  3. customwas performed at room temperature
  4. filtrationThe obtained white precipitate was filtered
  5. customdried under reduced pressure
  6. customthe yield was 135.5 g (yield rate of 99.9%)
  7. temperatureby heating
  8. temperaturecooled
  9. customAs a result, white crystal was obtained
  10. custom(112.6 g, yield rate of 83.8%)

출처 및 근거

ORD 기록
ord-583aca9cef9f473ba95af1cb6bdb9c66
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07867581B2

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