Acetaldehyde → Naphthalen-1(2H)-one

HRID 462375ノート

反応式

HRID 462375 の反応式
[CH:1](=[O:3])[CH3:2].Cl.O1[CH2:9][CH2:8][CH2:7][CH2:6]1>O>[C:1]1(=[O:3])[C:9]2[C:8](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:7]=[CH:6][CH2:2]1

参加物

5

反応物 3

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran

生成物 1

HCID 12446728Naphthalen-1(2H)-one収率 52.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

The acetaldehyde intermediate (4) (2.1 g, 10 mmol) was taken up in tetrahydrofuran (200 mL), and water (0.5 mL) and concentrated hydrochloric acid (1.0 mL) were added. The solution was heated at reflux for 5 hrs., then diluted with water (20 mL) and evaporated at reduced pressure to remove most of the tetrahydrofuran. The residual aqueous solution was extracted with ether (3×200 mL), and the combined ether extracts were successively washed with saturated sodium bicarbonate solution (20 mL), brine (50 mL), then dried and concentrated to give a semisolid. Recrystallization from benzene hexane provided 1.0 g (52.1%) of compound (5). mp 86°-91° C., 1H NMR (CDCl3) δ7.04-6.78 (m, 1H), 6.12-5.84 (m, 1H), 2.60-1.0 (m, 11H), 2.16 (s, 3H); mass spectrum, m/z 192 (M+).

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 5 hrs
  3. customevaporated at reduced pressure
  4. customto remove most of the tetrahydrofuran
  5. extractionThe residual aqueous solution was extracted with ether (3×200 mL)
  6. washthe combined ether extracts were successively washed with saturated sodium bicarbonate solution (20 mL), brine (50 mL)
  7. customdried
  8. concentrationconcentrated
  9. customto give a semisolid
  10. customRecrystallization from benzene hexane

出典と根拠

ORDレコード
ord-70b2cac6bd724b0fb8edae8af973c523
出典データセット
uspto-grants-1985_05
特許番号
US04515720

反応ノート

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