Formaldehyde → Benzaldehyde, 2-hydroxy-5-nonyl-

HRID 257241

반응식

HRID 257241 반응식
[CH3:1][O-:2].[Mg+2].C[O-].[CH2:6]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C=O.S(=O)(=O)(O)O>CO.C1(C)C=CC=CC=1.O>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:20][C:19]=1[CH:1]=[O:2]

참가 물질

8

반응물 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 17524-NonylphenolHCID 164537Methanol, magnesium salt (2:1)

생성물 1

HCID 114222Benzaldehyde, 2-hydroxy-5-nonyl-수율 94.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A solution of magnesium methoxide (292 g of 8% solution in methanol, 0.275 mol) was added over 10 minutes to a stirred solution of p-nonylphenol (55 g, 0.25 mol) in methanol (50 ml). The stirred mixture was heated to reflux temperature, the bulk of the methanol was removed by distillation, toluene (500 ml) was added and toluene:methanol azeotrope was removed by fractional distillation until the temperature of the reaction mixture rose to 100° C. The mixture was cooled to 90° C. and an agitated slurry of paraformaldehyde fine powder (26.25 g, 0.875 mol) in toluene (100 ml) was added evenly over 1 hour to the reaction mixture at 90°-100° C. with removal of volatile by-products by distillation. Stirring was continued at 100° C. for a further hour, the mixture was cooled to 45° C. and was added to a premixed solution of concentrated sulphuric acid (62.5 g, 0.875 mol) in water (1 liter). The resulting mixture was stirred at ambient temperature for 1 hour, the phases were separated and the aqueous phase was extracted with toluene (200 ml). The toluene extract was combined with the original organic phase and toluene was removed by distillation under reduced pressure to give the crude 2-hydroxy-5-nonyl benzaldehyde as a yellow oil (58.5 g).

후처리

  1. temperatureThe stirred mixture was heated
  2. temperatureto reflux temperature
  3. customthe bulk of the methanol was removed by distillation, toluene (500 ml)
  4. additionwas added
  5. customtoluene:methanol azeotrope was removed by fractional distillation until the temperature of the reaction mixture
  6. customrose to 100° C
  7. waitwas continued at 100° C. for a further hour
  8. temperaturethe mixture was cooled to 45° C.
  9. stirringThe resulting mixture was stirred at ambient temperature for 1 hour
  10. customthe phases were separated
  11. extractionthe aqueous phase was extracted with toluene (200 ml)
  12. extractionThe toluene extract
  13. customwas removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-29babf2567374a8abe49a27eeaaa1140
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260487

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