Hydrochloric Acid → HCID 18351607, compound

HRID 1604643Notes

Reaction equation

HRID 1604643 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:2]=1[O:1][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8991o-VanillinHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 18351607HCID 18351607, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-hydroxy-3-methoxybenzaldehyde (3.04 g), ethyl 2-bromopropionate (5.85 g), and potassium carbonate (4.14 g) in dimethylsulfoxide (20 ml) was stirred at 70° C. for 5 hours. The mixture was diluted with water, neutralized with 1N hydrochloric acid, and was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated. The crude product (0.93 g) was purified on a silica gel column (60 g) eluting with a mixed solvent of n-hexane and toluene (from 6:1 to 5:1) to give ethyl 2-(2-formyl-6-methoxyphenoxy)-propionate (5.25 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product (0.93 g) was purified on a silica gel column (60 g)
  7. washeluting with a mixed solvent of n-hexane and toluene (from 6:1 to 5:1)

Sources & evidence

ORD record
ord-a87904f226564f1ca66268638b1be302
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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