Potassium tert-butoxide → HCID 66846776, compound

HRID 1466636Notes

Reaction equation

HRID 1466636 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][CH2:19]Cl)=[C:12]([CH:16]=1)[C:13]([O-:15])=[O:14]>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH:18]=[CH2:19])=[C:12]([CH:16]=1)[C:13]([O:15][CH3:1])=[O:14]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86668385HCID 86668385, compound

Product 1

HCID 66846776HCID 66846776, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (40.4 g, 0.36 mol) was added portionwise to a solution of 5-chloro-2-(2-chloroethoxy)benzoate (76 g, 0.3 mol) in 600 mL of THF at 0° C. After stirring at that temperature for 1 hour, TLC showed complete consumption of starting material and the mixture was poured into ice water. The aqueous layer was extracted twice with EtOAc (200 mL), and the combined organics were evaporated to dryness. The residue was purified by silica gel column chromatography (Hexanes/EtOAc=50:1-30:1) to afford 22 g (34%) of methyl 5-chloro-2-(vinyloxy)benzoate. 1H NMR (400 MHz, CDCl3) δ: 7.76 (d, 1H), 7.38 (dd, 1H), 7.00 (d, 1H), 6.52 (dd, 1H), 4.67 (dd, 1H), 4.44 (dd, 1H), 3.83 (s, 3H).

Workup

  1. customconsumption of starting material
  2. additionthe mixture was poured into ice water
  3. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
  4. customthe combined organics were evaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (Hexanes/EtOAc=50:1-30:1)

Sources & evidence

ORD record
ord-3541639fbce64139956d4818f9363832
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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