Water → 3,4-Bis(dodecyloxy)benzaldehyde

HRID 1176969Notes

Reaction equation

[C:1]([O-:4])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1O)[CH:24]=[O:25].O>CN(C=O)C>[CH2:8]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:4][CH2:1][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])[CH:24]=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

K2CO3 (50.03 g, 0.362 mol) and 1-bromododecane (90.3 g, 0.362 mol) were added to a solution of 3,4-dihydroxybenzaldehyde (25.0 g, 0.181 mol) in 500 mL of DMF. The reaction mixture was heated at 100° C. for 2 days. The mixture was poured into H2O and extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was recrystallized from MeOH to give an off-white solid (64.8 g, 72.8%). mp 69-70° C. 1H NMR (200 MHz, CDCl3, δ): 9.80 (s, 1H), 7.36-7.41 (m, 2H), 6.92 (d, J=8.6 Hz, 1H), 4.03 (q, J=6.2 Hz, 4H), 1.81 (m, 4H), 1.44 (m, 4H), 1.24 (s, 32H), 0.85 (t, J=6.4 Hz, 6H). 13C{1H} NMR (200 MHz, CDCl3, δ): 190.92, 154.65, 149.42, 129.85, 126.54, 111.72, 110.93, 69.08, 31.89, 29.58, 29.34, 29.04, 28.96, 25.92, 22.66, 14.07. IR (cm−1): 2916, 2847, 1686, 1672, 1584, 1506, 1277, 1236, 1133, 807, 800. HRMS-FAB (m/z): [M+H]+ calcd for C31H55O3, 475.4151; found, 475.4156. Anal. Calcd for C31H54O3: C, 78.43; H, 11.46. Found: C, 78.46; H, 11.72.

Workup

extractionextracted with CH2Cl2
dry with materialThe organic layer was dried over anhydrous MgSO4
customThe solvent was removed under reduced pressure
customThe crude product was recrystallized from MeOH

Sources & evidence

ORD record: ord-e7eadd41ca0d46ef8b9c1b58110e2a86
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842830B2

Reaction notes

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