Benzaldehyde → 2,4-Pentanedione, 3-(phenylmethylene)-

HRID 714152

반응식

HRID 714152 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[CH:8](=[C:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 3

HCID 240BenzaldehydeHCID 962WaterHCID 31261Acetylacetone

생성물 1

HCID 957822,4-Pentanedione, 3-(phenylmethylene)-수율 95.3%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 8082Piperidine촉매HCID 241Benzene용매

실험 절차

2,4-Pentanedione (2, 4.10 ml, 39.2 mmol) and benzaldehyde (1b, 4.06 ml, 40.0 mmol) were stirred in benzene (10 ml). Piperdine (3 drops) and glacial acetic acid (6 drops) were added and the mixture refluxed with a Dean-Stark water trap for 3 hr. The resulting mixture was cooled to room temperature, extracted into ethyl ether, washed with hydrochloric acid (1 N), saturated sodium bicarbonate, hydrochloric acid (1 N) and twice with water. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford an oil. The crude oil was distilled bulb to bulb to give 7.03 g (95%) of a yellow oil; [expected mp 165-167° C.]; 1H NMR: δ 2.24 (s, 3H), 2.38 (s, 3H), 7.35 (s, 5H), 7.45 (s, 1H); 13C NMR: δ 26.5, 31.6, 128.9, 129.6, 130.5, 132.8, 139.6, 142.7, 196.2, 205.3.

후처리

  1. extractionextracted into ethyl ether
  2. washwashed with hydrochloric acid (1 N), saturated sodium bicarbonate, hydrochloric acid (1 N) and twice with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford an oil
  7. distillationThe crude oil was distilled bulb to bulb

출처 및 근거

ORD 기록
ord-1147d756bf1f49ec8ea1156cf8c26aec
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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