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

HRID 1721742ノート

反応式

HRID 1721742 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59f504a61de04fd6a0eadaed20ac76f8
出典データセット
uspto-grants-1996_04
特許番号
US05512696

反応ノート

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