Acetic Acid → 1-Benzyl-2-chloromethylnaphthalene

HRID 1275420

반응식

HRID 1275420 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 221195731-Benzyl-2-chloromethylnaphthalene수율 32%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-703b44c124f74a87a1d4ca06178ead62
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06160175

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