Malonic Acid → 3-(4-(3-Butyl-2-phenylnaphthalen-1-yloxy)phenyl)acrylic acid

HRID 1992942Notes

Reaction equation

HRID 1992942 reaction equation
[CH2:1]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:7]([O:15][C:16]2[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].[C:30](O)(=O)[CH2:31][C:32]([OH:34])=[O:33].CO>N1CCCCC1.N1C=CC=CC=1>[CH2:1]([C:5]1[C:6]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:7]([O:15][C:16]2[CH:23]=[CH:22][C:19](/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 867Malonic AcidHCID 887MethanolHCID 860871264-[(3-Butyl-2-phenyl-1-naphthalenyl)oxy]benzaldehyde

Product 1

HCID 445800253-(4-(3-Butyl-2-phenylnaphthalen-1-yloxy)phenyl)acrylic acidYield 53.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

4-[(3-Butyl-2-phenyl-1-naphthalenyl)oxy]benzaldehyde (173) (0.14 g, 0.36 mmol) was heated with malonic acid (0.12 g, 1.09 mmol) and 1 drop of piperidine in pyridine at 85° C. overnight to give the crude product as a light yellow viscous oil, which upon trituration with 1% MeOH in hexanes, yielded 81 mg (53%) of the title compound (174) as a white solid. mp 160-161° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.76 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.40-1.55 (m, 2H), 2.60 (t, J=7.9 Hz, 2H), 6.26 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 7.14-7.19 (m, 2H), 7.20-7.30 (m, 3H), 7.35 (d, J=8.6 Hz, 2H), 7.37-7.42 (m, 1H), 7.46-7.56 (m, 2H), 7.70-7.77 (m, 2H), 7.91 (d, J=8.2 Hz, 1H). LCMS (APCI): m/z 423 (M+H)+, m/z 421 (M−H)−. Anal. Calc for C29H26O3.⅙H2O: C, 81.86; H, 6.24. Found: C, 81.86; H, 6.25.

Sources & evidence

ORD record
ord-98689ccfe80a48e88ad4eb7df9d519fe
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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