Benzaldehyde → HCID 13573803, 화합물

HRID 280377

반응식

HRID 280377 반응식
[OH:1][CH2:2][CH:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:10]1([C@@H:9]2[N:7]3[C:6](=[O:8])[CH2:5][CH2:4][CH:3]3[CH2:2][O:1]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 240BenzaldehydeHCID 1140TolueneHCID 5583595-(Hydroxymethyl)pyrrolidin-2-one

생성물 1

HCID 13573803HCID 13573803, 화합물수율 86%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 962Water용매

실험 절차

A mixture of 5-hydroxymethyl-2-pyrrolidone (85.0 g), benzaldehyde (98.0 g), p-toluenesulfonic acid (1.6 g) and toluene (500 ml) was heated to reflux using a Dean-Stark water separator and an oil bath, with vigorous stirring. After nine hours, the collection of water stopped and the cooled reaction mixture was washed with 5% sodium bicarbonate solution (2×50 ml), saturated sodium bisulfide solution (4×50 ml), water (2×50 ml) and brine (1×50 ml). The toluene solution was dried over andydrous magnesium sulfate and the solvent removed on a rotary evaporator. The residue obtained was distilled, 145°-150° C./0.1 mm Hg to give the title compound as an oil (129.0 g). [α]D =+269.6° (chloroform; c=1). TLC single spot at Rf =0.5 (silica gel, ethyl acetae-hexane; 4:1 UV and iodine).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. customthe collection of water
  4. customthe cooled reaction mixture
  5. washwas washed with 5% sodium bicarbonate solution (2×50 ml), saturated sodium bisulfide solution (4×50 ml), water (2×50 ml) and brine (1×50 ml)
  6. dry with materialThe toluene solution was dried over andydrous magnesium sulfate
  7. customthe solvent removed on a rotary evaporator
  8. customThe residue obtained
  9. distillationwas distilled, 145°-150° C./0.1 mm Hg

출처 및 근거

ORD 기록
ord-a737217631a3430981672bf8baa63b2d
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588819

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