Water → HCID 22012434, compound

HRID 1533269Notes

Reaction equation

HRID 1533269 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([OH:14])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 870201,4-Benzodioxan-6-ylacetic acid

Product 1

HCID 22012434HCID 22012434, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,4-benzodioxane-6-acetic acid (5.0 g) and potassium carbonate (2.13 g) in dimethylformamide (20 ml) was added benzyl bromide (4.84 g) at room temperature. After being stirred at the same temperature for 3 hours, the mixture was poured into water (200 ml) and extracted with diethyl ether (150 ml). The organic layer was washed with 5% hydrochloric acid solution, 1M aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to afford benzyl 1,4-benzodioxane-6-acetate (7.08 g) as an oil.

Workup

  1. extractionextracted with diethyl ether (150 ml)
  2. washThe organic layer was washed with 5% hydrochloric acid solution, 1M aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54b7586d10224855a0b270d6e29e1323
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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