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Water → 3,4-Bis(dodecyloxy)benzaldehyde

HRID 1176969
Notes
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Reaction equation

HRID 1176969 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 87683,4-DihydroxybenzaldehydeHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 27249313,4-Bis(dodecyloxy)benzaldehydeYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes