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Acetic Acid → Methyl 6-fluoro-2-hydroxy-3,4-dihydro-1-naphthoate

HRID 1641039
ノート
印刷プレビュー

反応式

HRID 1641039 の反応式
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15](=[O:20])[CH2:14][CH2:13]2.C(O)(=O)C>C1(C)C=CC=CC=1.O>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:3]([O:6][CH3:7])=[O:8])=[C:15]([OH:20])[CH2:14][CH2:13]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

生成物 1

HCID 66735335Methyl 6-fluoro-2-hydroxy-3,4-dihydro-1-naphthoate収率 102.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

12.66 g (316 mmol) of 60% sodium hydride in oil, 900 ml of toluene and 17.69 ml (210 mmol) of dimethyl carbonate are introduced into a 2 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 19 g (115 mmol) of 6-fluoro-3,4-dihydro-1H-naphthalen-2-one in 350 ml of toluene is subsequently added. The reaction mixture is heated at reflux for 24 h. The reaction mixture is subsequently cooled to 0° C. and then acidified by addition of 114 ml of acetic acid. 114 ml of water are added and the separated organic phase is separated by settling and washed with two times 150 ml of water and then with 100 ml of a saturated aqueous sodium chloride solution. The organic phase is subsequently dried over magnesium sulphate and then concentrated under reduced pressure to result in 26.1 g of a product which is used as is in the following stage.

後処理

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 24 h
  4. customthe separated organic phase is separated
  5. washwashed with two times 150 ml of water
  6. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-959164c965a24b5383bcc08d72cecf07
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114899B2

反応ノート

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