ChemicalBook CAS DataBase List Dihydrocaffeic acid

Dihydrocaffeic acid synthesis

11synthesis methods

Product Name:Dihydrocaffeic acid
CAS Number:1078-61-1
Molecular formula:C9H10O4
Molecular Weight:182.17

331-39-5 Synthesis

331-39-5
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1078-61-1
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$6.00/1g

Yield:1078-61-1 95%

Reaction Conditions:

with 10% palladium on activated charcoal;hydrogen in acetone at 20; for 3 h;

Steps:

4.6. Preparation of saturated caffeic acid (22)
Five percentage palladium on activated carbon (20 mg) was added to caffeic acid (2, 100 mg) in acetone (l mL). The heterogeneous mixture was stirred under a hydrogen atmosphere at room temperature for 3 h. The mixture was filtered through celite which afforded a saturated caffeic acid (22, 95 mg, 95%) as a brown crystal.Saturated caffeic acid (= 3-(3,4-Dihydroxyphenyl)propanoic acid) (22): IR ν_max (film) 1715 cm^-1; ¹H NMR (CD₃OD, 500 MHz): δ 6.62 (1H, d, J = 7.6 Hz; H-5'), 6.59 (1H, d, J = 1.5 Hz; H-2'), 6.48 (1H, dd, J = 7.6, 1.5 Hz; H-6'), 2.71 (2H, t, J = 7.6 Hz; H-3), 2.47 (2H, t, J = 7.6 Hz; H-2); EIMS m/z 182 [M]⁺, 123 (base).

References:

Aung, Hnin Thanda;Furukawa, Tadashi;Nikai, Toshiaki;Niwa, Masatake;Takaya, Yoshiaki [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 7,p. 2392 - 2396] Location in patent:experimental part

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2107-70-2 Synthesis