Methanol → HCID 21437423, compound

HRID 1606220Notes

Reaction equation

HRID 1606220 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.), γ 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.), γ max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)

Sources & evidence

ORD record
ord-7901c145e9cb443e850c3bac5a93b1f7
Source dataset
uspto-grants-1976_04
Patent number
US03952033

Reaction notes

Loading…