Acetic Acid → 1-Benzyl-2-chloromethylnaphthalene

HRID 1275420

反応式

HRID 1275420 の反応式
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]C=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:20](O)(=O)[CH3:21].[ClH:24].P(=O)(O)(O)O>O>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:20]=1[CH2:21][Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 380741-Benzylnaphthalene

生成物 1

HCID 221195731-Benzyl-2-chloromethylnaphthalene収率 32%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

1-Benzylnaphthalene (3.0 g; 13.7 mMol), as prepared above, formaldehyde (1.0 g; 35.7 mMol), glacial acetic acid (4.3 g; 71.7 mMol), concentrated hydrochloric acid (6.5 mL) and 85% phosphoric acid (4.3 mL) were combined and heated in an oil bath maintained at 90° C. for 4.5 hr. The reaction mixture was cooled, a small amount of water was added, and extraction was carried out with diethyl ether. The combined organic extractions were washed with sodium carbonate (10% aqueous), and brine; then dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue subjected to medium pressure chromatography on silica gel eluting with hexane. The product (1.18 g; 32% yield) was isolated as a colorless oil which subsequently crystallized.

後処理

  1. temperatureheated in an oil bath
  2. temperatureThe reaction mixture was cooled
  3. extractionextraction
  4. extractionThe combined organic extractions
  5. washwere washed with sodium carbonate (10% aqueous), and brine
  6. dry with materialthen dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe product (1.18 g; 32% yield) was isolated as a colorless oil which
  9. customsubsequently crystallized

出典と根拠

ORDレコード
ord-703b44c124f74a87a1d4ca06178ead62
出典データセット
uspto-grants-2000_12
特許番号
US06160175

関連ノート

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