Sodium Chloride → 1-(Dodecyloxy)-4-vinylbenzene

HRID 1176172Notes

Reaction equation

HRID 1176172 reaction equation
[Li][CH2:2]CCC.[CH2:6]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[Na+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:6]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH2:2])=[CH:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 141069p-DodecyloxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 6400011-(Dodecyloxy)-4-vinylbenzene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To Methyltriphenylphosphonium bromide (8.13 g, 2.28×10−2 mol) in 60 ml of dry THF was added n-BuLi (1.6 M solution in hexane, 15.8 ml, 2.53×10−2 mol) dropwise at −78° C. After 2.5 h, the reaction mixture was gradually warmed up to 0° C., and again cooled to −78° C. 4-Dodecyloxybenzaldehyde (6.00 g, 2.07×10−2 mol) in 20 ml of dry THF was slowly added to the reaction mixture. The reaction mixture was stirred overnight and meanwhile gradually warmed up to 10° C. Aqueous NaCl was added to the reaction mixture and the organic layer was extracted with petroleum ether. The organic layer was dried over Na2SO4. After the solvent was evaporated, the residue was chromatographed on silica gel with 1:1 hexane:CH2Cl2. Yield=5.358 g (90% based on 6.00 g of 4-dodecyloxybenzaldehyde). 1H NMR (250 MHz, CDCl3): δ 7.33 (d, 2H, J=8.7 Hz, Ph), 6.85 (d, 2H, J=8.7 Hz, Ph), 6.66 (dd, 1H, J=10.8, 17.6 Hz, vinyl-H), 5.60 (d, 1H, J=17.5 Hz, vinyl-H), 5.11 (d, 1H, J=10.6 Hz, vinyl-H), 3.95 (t, 2H, J=6.6 Hz, OCH2), 1.78 (quint, 2H, J=7.0 Hz, OCH2CH2), 1.38-1.52 (m, 2H, —CH2—), 1.16-1.38 (m, 16H, —CH2—), 0.88 (t, 3H, J=6.6 Hz, —CH3). CI MS m/z: 288.245 (M+) (calcd 288.245).

Workup

  1. temperatureagain cooled to −78° C
  2. temperaturemeanwhile gradually warmed up to 10° C
  3. extractionthe organic layer was extracted with petroleum ether
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customAfter the solvent was evaporated
  6. customthe residue was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-3dab0ad720854cc796fad5997ac1b813
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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