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Hydrochloric Acid → 2-(2-Hydroxy-5-methoxyphenyl)-4-methoxyphenol

HRID 1077603
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1077603
[OH:1][C:2]1[C:7](C(C)(C)C)=[CH:6][C:5]([O:12][CH3:13])=[CH:4][C:3]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16](C(C)(C)C)[C:15]=1[OH:26].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[OH:26][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:3]1[CH:4]=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][C:2]=1[OH:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1192343,3'-Bis(1,1-dimethylethyl)-5,5'-dimethoxy(1,1'-biphenyl)-2,2'-diol2×HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 100147912-(2-Hydroxy-5-methoxyphenyl)-4-methoxyphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Part A: 2,2'-dihydroxy-5,5'-dimethyoxy-1,1'-biphenyl was prepared by the dealkylation of 2,2'-dihydroxy-3,3'-di-t-butyl-5,5'-dimethyoxy-1,1'-biphenyl using a procedure described by Tashiro, M.; Fukata, G., and Yamato, T.; Organic Preparations and Procedures Int., 8, 263 (1976). AlCl3 (10 g) and 10 g of 2,2'-dihydroxy-3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl were mixed in 125 ml of benzene and heated at 40° C. for 3 h. The mixture was cooled in ice and 125 ml of 10% HCl solution was added slowly. The organic layer was separated and washed with 3×125 ml of 10% NaOH. The basic solution was neutralized with concentrated HCl and extracted with 3×100 ml of ether. The ether layer was dried over Na2SO4. After filtering and removing the solvent by vacuum evaporation, the brown oil was washed with hexane and then the product crystallized from CH2Cl2 /hexane. 2.202 g of 2,2'-dihydroxyl-5,5'-dimethoxy-1,1'-biphenyl was obtained as a white solid. 1H nmr (300 MHz, CD2Cl2): 6.9-6.8 (m, 6H), 5.71 (s, 2H), 3.78 (s, 6H).

Aufarbeitung

  1. temperatureThe mixture was cooled in ice
  2. customThe organic layer was separated
  3. washwashed with 3×125 ml of 10% NaOH
  4. extractionextracted with 3×100 ml of ether
  5. dry with materialThe ether layer was dried over Na2SO4
  6. filtrationAfter filtering
  7. customremoving the solvent
  8. customby vacuum evaporation
  9. washthe brown oil was washed with hexane
  10. customthe product crystallized from CH2Cl2 /hexane

Quellen und Nachweise

ORD-Eintrag
ord-d03c39867e3d4971be6e2519ae8c27cd
Quelldatensatz
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05543536

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