Benzaldehyde → Dicinnamoylmethane

HRID 714150

Reaction equation

HRID 714150 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.B(OCCCC)(OCCCC)O[CH2:18][CH2:19][CH2:20]C.[CH2:32](N)[CH2:33][CH2:34][CH3:35].Cl>C(OCC)(=O)C>[C:9]1([CH:8]=[CH:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH:5]=[CH:35][C:34]2[CH:20]=[CH:19][CH:18]=[CH:32][CH:33]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8007ButylamineHCID 12712Tributyl borateHCID 31261Acetylacetone

Product 1

HCID 390472DicinnamoylmethaneYield 162.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boric anhydride (0.49 g, 7.0 mmol) was combined with 2,4-pentanedione (2, 1.05 ml, 10.0 mmol) and stirred for 18 hr at room temperature under a nitrogen atmosphere. A solution of dry ethyl acetate (10 ml), benzaldehyde (1b, 2.05 g, 20.2 mmol) and tributyl borate (11.00 ml, 40.5 mmol) was added and the mixture stirred for 15 min at room temperature. Butylamine (0.20 ml, 2.0 mmol) was added dropwise over 30 min and stirring was continued for 18 hr at room temperature. Hydrochloric acid (15 ml, 0.4 N) was warmed to 60° C., added to the mixture and stirring was continued for 1 hr. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was triturated with methanol to give 0.90 g (33%) of a yellow solid: mp 140-142° C. [expected mp 139-140° C.]; 1H NMR: δ 5.84 (s, 1H), 6.62 (d, 2H, J=15.7 Hz), 7.39 (m, 6H), 7.54 (dd, 4H, J=7.4, 4.0 Hz), 7.66 (d, 2H, J=15.9 Hz), 15.85 (s, 1H); 13C NMR: δ 101.6, 124.1, 128.0, 128.9, 130.0, 135.0, 140.5, 183.2.

Workup

  1. stirringthe mixture stirred for 15 min at room temperature
  2. stirringstirring
  3. waitwas continued for 18 hr at room temperature
  4. additionadded to the mixture
  5. stirringstirring
  6. waitwas continued for 1 hr
  7. extractionThe resulting mixture was extracted into ethyl acetate
  8. washwashed with saturated sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto afford a solid
  13. customThe crude solid was triturated with methanol

Sources & evidence

ORD record
ord-5cef2e3ff9424e088c23d20ae02d39ca
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Linked notes

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