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

HRID 496322노트

반응식

HRID 496322 반응식
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

참가 물질

8

반응물 6

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

생성물 1

HCID 136680487-Methylnaphthalene-1-carboxylic acid

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.)

출처 및 근거

ORD 기록
ord-3066a6f27bb9496095149d8dfc7fd85a
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943267B1

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