Water → 2,3-Bis(1-phenyl-1-hydroxymethyl)naphthalene

HRID 461444

反応式

HRID 461444 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[C:2]=1[CH:13]=[O:14].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[C:15]1([CH:13]([C:2]2[C:3]([CH:11]([OH:12])[C:1]3[CH:10]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[OH:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 962WaterHCID 964002,3-NaphthalenedicarboxaldehydeHCID 178418255HCID 178418255、化合物

生成物 1

HCID 213937502,3-Bis(1-phenyl-1-hydroxymethyl)naphthalene収率 86.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2,3-Naphthalenedicarboxaldehyde (10.0 g) in dry tetrahydrofuran (100ml) was added to phenylmagnesium bromide [derived from bromobenzene (53 g) and magnesium (8 g)] in dry tetrahydrofuran (500 ml) over 1 hr. and the solution was refluxed for a further 3 hr. On cooling, water (500 ml) was added and the ethereal layer was decanted. The aqueous slurry was washed with ether (4 × 500 ml) and the combined ethereal extracts were dried (magnesium sulphate) and evaporated to dryness. The residue was purified by chromatography on silica gel and recrystallised from dichloromethane/petroleum ether (b.p. 40°-60°) to yield two isomers of 2,3-bis(1-phenyl-1-hydroxymethyl)naphthalene (III) (8.0 g. m.p. 145° and 3.0 g, m.p. 164°).

後処理

  1. temperatureand the solution was refluxed for a further 3 hr
  2. temperatureOn cooling
  3. customthe ethereal layer was decanted
  4. washThe aqueous slurry was washed with ether (4 × 500 ml)
  5. dry with materialthe combined ethereal extracts were dried (magnesium sulphate)
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on silica gel
  8. customrecrystallised from dichloromethane/petroleum ether (b.p. 40°-60°)

出典と根拠

ORDレコード
ord-ec42555b67f34b5e82c0293fffbf1762
出典データセット
uspto-grants-1977_12
特許番号
US04062955

関連ノート

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