Acetic Acid → 1-Benzyl-2-chloromethylnaphthalene
Reaction equation
[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]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
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.
Workup
- temperatureheated in an oil bath
- temperatureThe reaction mixture was cooled
- extractionextraction
- extractionThe combined organic extractions
- washwere washed with sodium carbonate (10% aqueous), and brine
- dry with materialthen dried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- customThe product (1.18 g; 32% yield) was isolated as a colorless oil which
- customsubsequently crystallized
Sources & evidence
- ORD record
- ord-703b44c124f74a87a1d4ca06178ead62
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06160175
Reaction notes
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