2-Methylnaphthalene → 7-Methylnaphthalene-1-carboxylic acid

HRID 496322Notes

Reaction equation

HRID 496322 reaction equation
P([O-])(OC)[O:2]C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.CC1C=CC2C(=CC=CC=2)C=1.[CH3:40][C:41]1[CH:50]=[C:49]2[C:44]([CH:45]=[CH:46][CH:47]=[C:48]2[C:51](=[O:53])C)=[CH:43][CH:42]=1.BrBr.COP(OC)(OC)=S>C1C=CC=CC=1>[CH3:40][C:41]1[CH:50]=[C:49]2[C:44]([CH:45]=[CH:46][CH:47]=[C:48]2[C:51]([OH:53])=[O:2])=[CH:43][CH:42]=1

Participants

8

Reactant 6

HCID 70552-MethylnaphthaleneHCID 9038O,O,O-trimethyl phosphorothioateHCID 24408BromineHCID 87949Lawesson's reagentHCID 101979691-(7-Methylnaphthalen-1-yl)ethan-1-oneHCID 21884954Dimethylphosphite

Product 1

HCID 136680487-Methylnaphthalene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-Iodopropane and benzyl chloride were commercial products. 6-Bromohexanoic acid tert-butyl ester was synthesized by passing isobutylene through solution of 6-bromohexanoic acid in dichlomethane in presence of concentrated sulfuric acid (See, Lecher, H. Z., Greenwood, R. A., Whitehouse, K. C. and Chao, T. H. “The Phosphonation of Aromatic Compounds with Phosphorus Pentasulfide.” J. Am. Chem. Soc. 78, (1956) 5018-5022.) and used directly without purification in the next step of the synthetic process. Dimethyl thiophosphite was produced by refluxing dimethyl phosphite (Sigma-Aldrich, St. Louis, Mo.) with Lawesson's reagent in benzene. (Snatzke, G. and Kunde, K. “Perhydrodibenz[a.j]anthracen-14-one, I. Synthese 2-substituierter Dibenz[a.j]anthracen-Derivate.” Chem. Ber. 106, (1973) 1341-1362) 7-Methylnaphthalene-1-carboxylic acid was prepared by acetylation of 2-methylnaphthalene to 1-(7-methyl-naphthalen-1-yl)-ethanone followed by oxidation with bromine. (See, Hilgetag, G. and Teichmann, H. “Uber einige Methylierungsreactionen der beiden isomeren Trimethylthiophosphate.” J. Prakt. Chem. 8, (1959) 90-96.)

Sources & evidence

ORD record
ord-3066a6f27bb9496095149d8dfc7fd85a
Source dataset
uspto-grants-2005_09
Patent number
US06943267B1

Reaction notes

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