Phenol → Phenyl 3-phenylprop-2-enoate

HRID 251783

反応式

HRID 251783 の反応式
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

参加物

8

反応物 4

HCID 996PhenolHCID 8471TriethylamineHCID 785207Phenyl CinnamateHCID 5354261Cinnamoyl Chloride

生成物 1

HCID 95152Phenyl 3-phenylprop-2-enoate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-583aca9cef9f473ba95af1cb6bdb9c66
出典データセット
uspto-grants-2011_01
特許番号
US07867581B2

関連ノート

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