2-Methoxynaphthalene → 3-Phenoxyphenyl ethyl ketone

HRID 2419890Notes

Reaction equation

HRID 2419890 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)C=[C:8](C(C)C(C1C=CC=CC=1)=O)[CH:7]=[CH:6]2.CO[C:25]1[CH:26]=[C:27]2C(=[CH:33][CH:34]=1)C=CC=C2.C(Cl)(=[O:38])CC.[Cl-].[Al+3].[Cl-].[Cl-].C(C(C1C=CC2C(=CC=C(OC)C=2)C=1)=O)C.C(OC)(OC)OC.C(C(C1C=CC=C(O)C=1)=O)C.C1(Br)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:7]([C:6]([C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([O:2][C:1]2[CH:27]=[CH:26][CH:25]=[CH:34][CH:33]=2)[CH:4]=1)=[O:38])[CH3:8]

Participants

11

Reactant 9

HCID 71192-MethoxynaphthaleneHCID 7961BromobenzeneHCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 759131-(6-Methoxy-2-naphthalenyl)-1-propanoneHCID 831413'-HydroxypropiophenoneHCID 6451240Aluminum(III) ChlorideHCID 706061826-Methoxy-2-naphthyl propiophenone

Product 1

HCID 108679943-Phenoxyphenyl ethyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For the preparation of the preferred aryl alkyl ketones a Friedel-Crafts reaction can be used, e.g., to effect reaction according to the following general format ##STR7## wherein R" is the residue of the desired aryl (Ar) group and R1 is the residue of the carboxylic acyl halide. For example, the 6-methoxy-2-naphthyl propiophenone can be prepared by reacting 6-methoxynaphthalene with propionyl chloride in the presence of aluminum chloride in methylene chloride. The resulting 6-methoxy-2-naphthyl ethyl ketone is converted to the ketal starting material for this process by reacting it with trimethyl orthoformate in the presence of acid. The 3-phenoxyphenyl ethyl ketone ketal can be prepared by reacting 3-hydroxyphenyl ethyl ketone with phenyl bromide in the presence of potassium carbonate to form 3-phenoxyphenyl ethyl ketone and then reacting this ketone with trimethylorthoformate to form the ketal. The ketal of 2-fluoro-4-biphenylyl ethyl ketone is formed by reacting 2-fluoro-4-biphenylyl ethyl ketone with trimethylorthoformate to form the ketal. The 2-fluoro-4-biphenylyl ethyl ketone can be prepared from 4-bromopropiophenone via 4'-bromo-3'-nitropropiophenone (see Chemical Abstracts, 61, p. 8232g), 4-propionyl-2-nitrobiphenyl (Ullman reaction), 4-propionyl-2-aminobiphenyl (reduction) and finally the Schiemann Reaction. See U.S. Pat. No. 3,793,457, Example 1 for a similar synthesis of 2-fluoro-4-biphenyl methyl ketone. The difluorobiphenyl ketone can be prepared by reacting 4-cyano-2,2'-difluorobiphenyl with ethyl magnesium bromide to form the di-fluoro biphenylyl ethyl ketone. See U.S. Pat. No. 3,755,427. This ketone can be converted to the ketal by the procedure described above.

Workup

  1. customa Friedel-Crafts reaction
  2. customreaction

Sources & evidence

ORD record
ord-b088cc04dfe040b6adaccad90d15625f
Source dataset
uspto-grants-1978_08
Patent number
US04107439

Reaction notes

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