Hexane → Methyl 4-ethenylbenzoate

HRID 2172141Notes

Reaction equation

HRID 2172141 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=1.CCCCCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([O:8][CH3:7])=[O:18])=[CH:11][CH:12]=1)=[CH2:1]

Participants

6

Reactant 3

HCID 8058HexaneHCID 15294Methyl 4-FormylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 583124Methyl 4-ethenylbenzoateYield 76.2%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of methyltriphenylphosphonium bromide (10.88 g, 30.46 mmol, 1 eq.) and potassium tert-butoxide (31 mL, 1 M solution in THF, 30.46 mmol, 1 eq.) in THF is added methyl-4-formylbenzoate (5.0 g, 30.46 mmol, 1 eq.). The bright yellow reaction mixture is stirred at room temperature for 5 hrs. Hexane is added and after stirring for 10 minutes, the mixture is filtered and washed twice with hexanes. Solvent is removed in vacuum and the crude oily residue is purified by silica gel chromatography (0-14% ethyl acetate/hexanes) to give 3.76 g of a white oily solid, methyl 4-vinylbenzoate (23.21 mmol, 76.2% yield). 1H NMR (300 MHz, CDCl3): δ 7.99 (2H, d, J=9 Hz), 7.45 (2H, d, J=9 Hz), 6.76 (1H, dd, J=17, 11 Hz), 5.86 (1H, d, J=17 Hz), 5.37 (1H, d, J=11 Hz), 3.91 (3H, s).

Workup

  1. stirringafter stirring for 10 minutes
  2. filtrationthe mixture is filtered
  3. washwashed twice with hexanes
  4. customSolvent is removed in vacuum
  5. customthe crude oily residue is purified by silica gel chromatography (0-14% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-db13cbc0c94b48259134904b28ef7bdb
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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