1,2-Dimethoxyethane → HCID 58566423, compound

HRID 2177316Notes

Reaction equation

HRID 2177316 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1/[CH:10]=[CH:11]\[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(NN)(C1C=CC(C)=CC=1)(=O)=O.CC([O-])=O.[Na+].COCCOC>O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 15303P-ToluenesulfonylhydrazideHCID 517045Sodium AcetateHCID 131733001HCID 131733001, compound

Product 1

HCID 58566423HCID 58566423, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL round-bottom flask, was placed ethyl (2Z)-3-(2,3-dichloro-4-hydroxyphenyl)prop-2-enoate (270 mg, 1.03 mmol, 1.00 equiv), TsNHNH2 (193 mg, 1.04 mmol, 1.00 equiv), NaOAc (424 mg, 5.17 mmol, 5.00 equiv), ethylene glycol dimethyl ether (10 mL), water (1 mL). The resulting solution was stirred overnight at 80° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3). This resulted in 150 mg (52%) of ethyl 3-(2,3-dichloro-4-hydroxyphenyl)propanoate as a red solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 150 mg (52%) of ethyl 3-(2,3-dichloro-4-hydroxyphenyl)propanoate as a red solid

Sources & evidence

ORD record
ord-df6142f5adf44288ba1977d8261ee57a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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