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

HRID 77637

Reaction equation

HRID 77637 reaction equation
[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

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 31261Acetylacetone

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8755114f947d4444af80e019f14ce045
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Linked notes

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