Diethyl Ether → HCID 11321926, compound

HRID 964870Notes

Reaction equation

HRID 964870 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:11](Br)[CH:12]=[CH2:13].[C:15](=O)([O-])[O-].[K+].[K+].CCO[CH2:24][CH3:25]>CN(C)C=O>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:15][CH:24]=[CH2:25])=[O:6])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74203-Hydroxybenzoic AcidHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 11321926HCID 11321926, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (7.24 mmol) of 3-hydroxybenzoic acid, 3.0 g (25.3 mmol) of allyl bromide, and 5 g (36.2 mmol) of potassium carbonate in 4 mL of N,N-dimethylformamide is stirred at room temperature for 12 hours. The mixture is diluted with 20 mL of ether and washed five times with 20 mL of water. The organic layer is then washed successively with 20 mL of saturated sodium bicarbonate solution and 20 mL of saturated sodium chloride solution. The organic layer is separated and dried over magnesium sulfate. The mixture is filtered and the organic solution is concentrated in vacuo to give 1.4 g (88%) of 3-(2-propenyloxy)benzoic acid, 2-propenyl ester as a clear colorless oil. The product is utilized in the next reaction without further purification. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 1720, 1650, 1600 cm-1 ; MS (CI low res) m/e 219 (M+H), 203, 175, 161; Analysis calculated for C13H14O3 : C, 71.54; H, 6.47; found: C, 70.31; H, 5.97.

Workup

  1. washwashed five times with 20 mL of water
  2. washThe organic layer is then washed successively with 20 mL of saturated sodium bicarbonate solution and 20 mL of saturated sodium chloride solution
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture is filtered
  6. concentrationthe organic solution is concentrated in vacuo

Sources & evidence

ORD record
ord-f9b11554df0c43c1a58012a20de10b5d
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

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