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

HRID 714152

反応式

HRID 714152 の反応式
[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

参加物

7

反応物 3

HCID 240BenzaldehydeHCID 962WaterHCID 31261Acetylacetone

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 8082Piperidine触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1147d756bf1f49ec8ea1156cf8c26aec
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

関連ノート

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