Diethyl Ether → 4-Vinylbenzoic acid

HRID 428782

Reaction equation

HRID 428782 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[OH-].[Na+].C(OCC)C>C1COCC1.O>[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 583124Methyl 4-ethenylbenzoate

Product 1

HCID 140984-Vinylbenzoic acidYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a well-stirred solution of methyl p-vinylbenzoate (36.0 g, 0.222 mole) in THF (200 mL) was added a solution of sodium hydroxide (17.78 g, 0.444 mole) in water (200 mL) at room temperature. After stirring overnight, water (100 mL), THF (150 mL), and ethyl ether (200 mL) was added and the phases separated. The aqueous phase was acidified with a solution of concentrated hydrochloric acid (41 mL) in water (90 mL) then extracted three times with THF (500-600 mL each). The latter combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to provide 32.7 g (99.5 percent) of white solids. Proton nmr (Gemini model 300 MHz) in deuterochloroform: delta 8.08 (2H), 7.50 (2H), 6.78 (1H), 5.90 (1H), 5.41 (1H).

Workup

  1. customthe phases separated
  2. extractionthen extracted three times with THF (500-600 mL each)
  3. dry with materialThe latter combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0aeeedd0afab4e92ac9a1d754d9a4439
Source dataset
uspto-grants-2001_11
Patent number
US06313340B1

Linked notes

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