Methanol → HCID 21437423, compound

HRID 2397258Notes

Reaction equation

HRID 2397258 reaction equation
[C:1]([CH2:6][CH2:7][C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:13][OH:14].[C:15](=[O:18])([O-])[O-].[Na+].[Na+].BrBr>[Cl-].[Na+].O>[CH3:13][O:14][C:8]1([CH2:7][CH2:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:12]=[CH:11][CH:10]([O:18][CH3:15])[O:9]1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 10340Sodium CarbonateHCID 24408BromineHCID 61450Ethyl 2-furanpropionate

Product 1

HCID 21437423HCID 21437423, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 2-(2'-carbethoxyethyl)furan (42.5 g.) in 750 ml. of methanol containing 53 g. of sodium carbonate at -25° C. is added a solution of 40.5 g. of bromine in 250 ml. of methanol during the course of 2.5 hours. The solution is stirred at room temperature for 30 minutes, diluted with brine, and extracted with diethyl ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is distilled to provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group).

Workup

  1. customduring the course of 2.5 hours
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue is distilled
  7. customto provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)

Sources & evidence

ORD record
ord-48e8321e702941d09faec3debfb06cb6
Source dataset
uspto-grants-1977_05
Patent number
US04021452

Reaction notes

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