Formaldehyde → HCID 15531554、化合物

HRID 1062525ノート

反応式

HRID 1062525 の反応式
C([Mg]Br)C.[C:5]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:10]=1[OH:21])([CH3:8])([CH3:7])[CH3:6].[CH2:22]=[O:23].C(N(CC)CC)C>C1COCC1.C1(C)C=CC=CC=1>[C:5]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[C:11]([CH:22]=[O:23])[C:10]=1[OH:21])([CH3:8])([CH3:6])[CH3:7]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 162519[1,1'-Biphenyl]-4-ol, 3-(1,1-dimethylethyl)-HCID 178418443HCID 178418443、化合物

生成物 1

HCID 15531554HCID 15531554、化合物収率 78%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Into a 1 liter reactor thoroughly purged with nitrogen, 66.80 ml of an ether solution containing 200.4 mmol of ethylmagnesium bromide and 100 ml of THF were introduced. To the reactor, a solution containing 43.16 g (190.7 mmol) of 2-t-butyl-4-phenylphenol diluted with 90 ml of a THF was dropwise added at 0° C. over a period of 40 minutes, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 30 minutes. Then, 700 ml of toluene was added, and the system was heated to 100° C. to distill off 52 ml of a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to −20° C., 13.84 g (460.9 mmol) of paraformaldehyde and 38.1 ml (273.4 mmol) of triethylamine were added, followed by stirring at 90° C. for 30 minutes. After ice cooling, the reaction solution was quenched with 133 ml of 18% hydrochloric acid. The organic layer was washed with 300 ml of water, 300 ml of a sodium hydrogencarbonate aqueous solution and 300 ml of a sodium chloride aqueous solution, and then concentrated. The resulting liquid was purified by silica gel column chromatography to obtain 37.73 g (yield: 78%) of 3-t-butyl-5-phenylsalicylaldehyde.

後処理

  1. customInto a 1 liter reactor thoroughly purged with nitrogen, 66.80 ml of an ether solution
  2. additionwere introduced
  3. additionwas dropwise added at 0° C. over a period of 40 minutes
  4. temperaturethe system was heated to 100° C.
  5. distillationto distill off 52 ml of a mixed solution of ether and THF, whereby an opaque white slurry
  6. customwas obtained
  7. temperatureAfter the slurry was cooled to −20° C.
  8. stirringby stirring at 90° C. for 30 minutes
  9. customAfter ice cooling, the reaction solution was quenched with 133 ml of 18% hydrochloric acid
  10. washThe organic layer was washed with 300 ml of water, 300 ml of a sodium hydrogencarbonate aqueous solution and 300 ml of a sodium chloride aqueous solution
  11. concentrationconcentrated
  12. customThe resulting liquid was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f158801f322a450f8ac387fb3d2fdb21
出典データセット
uspto-grants-2005_11
特許番号
US06962890B2

反応ノート

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