1-Bromodecane → 3,4-didecoxybenzaldehyde

HRID 275174Notes

Reaction equation

HRID 275174 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[C:22]([O-:25])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:25][CH2:22][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[O:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate2×

Product 1

HCID 27249293,4-didecoxybenzaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,4-Dihydroxybenzaldehyde (10 g., 72.4 mmol, 1 equiv.) is dissolved in 150 mL of acetone. 1-Bromodecane (45.1 mL, 0.217 mol, 3 equiv.) is added, followed by K2CO3 (10 g., 72.4 mmol, 1 equiv.), and the mixture heated to reflux for 24 hrs. At this time the reaction was incomplete, and another 10 grams of K2CO3 was added and heating continued for 24 hours. The mixture is allowed to cool to room temperature, and is partitioned between ether and water. The aqueous layer is extracted thrice with ether, and the combined organic phases are washed with brine, dried (MgSO4), and evaporated. Upon evaporation, tan crystals formed, and these were collected. Further evaporation yielded another crop of crystals. A total of 16 grams of 3,4-didecyloxybenzaldehyde (38.3 mmol, 53%) was obtained (for an alternative synthesis of this compound see Strzelecka, H.; et al. Mol. Cryst. Liq. Cryst. 1988, 156 (Part A), 347): mp=59.5°-60.5° C.; UVmax (EtOH) 232 nm (ε=15472), 276 nm (ε=11079), 206 nm (ε=9806), 310 nm (ε=9273); 1H NMR (300 MHz, CDCl3) δ 9.81 (s, 1H, CHO), 7.39 (dd, J=2, 8 Hz, 1H, ArH), 7.37 (d, J=2 Hz, 1H, ArH), 6.93 (d, J=8 Hz, 1H, ArH), 4.04 (m, 4H, RCH2O), 1.83 (m, 4H, RCH2CH2O), 1.46 (m, 4H, decyl), 1.25 (m, 24H, decyl), 0.86 (m, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 190.98 (C=O), 154.68, 149.44, 129.87, 126.57, 111.76, 110.97, 69.13, 31.90, 29.57, 29.34, 29.07, 28.98, 25.97, 25.94, 22.68, 14.10; IR (KBr) 2956, 2922, 2850, 1688, 1674, 1596, 1586, 1510, 1278, 1134, 808 cm-1 ; MS (DCI) m/e 419 (MH+). Anal. Calcd for C27H46O3 : C, 77.46; H, 11.07. Found: C, 77.19; H, 10.99.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 24 hrs
  3. temperatureheating
  4. customis partitioned between ether and water
  5. extractionThe aqueous layer is extracted thrice with ether
  6. washthe combined organic phases are washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customUpon evaporation, tan crystals
  10. customformed
  11. customthese were collected
  12. customFurther evaporation
  13. customyielded another crop of crystals

Sources & evidence

ORD record
ord-5885e593251b4f0a8bf47df1910d8e50
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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