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

HRID 1721742
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1721742
[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

2,2'-Dihydroxyl-5,5'-dimethoxy-1,1'-biphenyl was prepared by the dealkylation of 2,2'-dihydroxy-3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl using a procedure described in the literature (Tashiro et al., Organic Preparations and Procedures Int., 8, 263, 1976). Ten grams of AlCl3 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 hours. The mixture was cooled in ice, and 125 ml of 10% aqueous HCl was added slowly. The organic layer was separated and washed with three 125-ml portions of 10% NaOH. The basic solution was neutralized with concentrated HCl and extracted three times with 100 ml portions 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; the product crystallized from CH2Cl2 /hexane, yielding 2.202 g of 2,2'-dihydroxy-5,5'-dimethyoxy-1,1'-biphenyl, which was obtained as a white solid. 1H (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 three 125-ml portions of 10% NaOH
  4. extractionextracted three times with 100 ml portions 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-59f504a61de04fd6a0eadaed20ac76f8
Quelldatensatz
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05512696

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