Hydrochloric Acid → 1-(4-Chlorophenyl)-4,4-difluorobutane-1,3-dione

HRID 129203

反応式

HRID 129203 の反応式
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].CO.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1.Cl>C(OCC)C>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:22][C:21]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)=[O:23]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7467P-ChloroacetophenoneHCID 9961Ethyl difluoroacetateHCID 10942334Sodium Methoxide

生成物 1

HCID 153380131-(4-Chlorophenyl)-4,4-difluorobutane-1,3-dione収率 99.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

Ethyl difluoroacetate (24.82 g, 200 mmol) was placed in a 500 mL three-necked round bottom flask, and dissolved in diethyl ether (200 mL). To the stirred solution was added 25 weight % sodium methoxide in methanol (48 mL, 210 mmol) via an addition funnel over a 2 minute period. Next, 4'-chloroacetophenone (25.94 g, 200 mmol) was dissolved in diethyl ether (50 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (18 hours), 1N HCl (250 mL) and ether (250 mL) were added. The organic layer was collected, washed with brine (250 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 46.3 g of a yellow solid. The solid was recrystallized from methylene chloride and iso-octane to give 31.96 g, 69% of the dione, mp 65°-66.5° C.

後処理

  1. additionadded to the reaction dropwise over 5 minutes
  2. additionwere added
  3. customThe organic layer was collected
  4. washwashed with brine (250 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f67765dc974c4588ba7228bd4f392c8b
出典データセット
uspto-grants-1995_11
特許番号
US05466823

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