Water → HCID 67516028, compound

HRID 2173336Notes

Reaction equation

HRID 2173336 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[O:15][CH3:16])(=[O:3])[CH3:2].C1C(=O)N([Cl:24])C(=O)C1.O>CN(C=O)C>[C:1]([O:4][C:5]1[C:6]([O:15][CH3:16])=[CH:7][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[C:9]([Cl:24])[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acid

Product 1

HCID 67516028HCID 67516028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of [4-(acetyloxy)-3-methoxyphenyl]acetic acid (650 mg, 2.90 mmol) in DMF (10 mL) was added a solution of NCS (428 mg, 3.192 mmol) in DMF (5 mL) dropwise at 0° C. The mixture was stirred at ambient temperature for 6 hrs, and then poured into water (100 mL) and extracted with EtOAc (3*100 mL). The combined organic layers were washed with 1 N HCl, brine, dried over Na2SO4 and then concentrated to obtain [4-(acetyloxy)-2-chloro-5-methoxyphenyl]acetic acid.

Workup

  1. extractionextracted with EtOAc (3*100 mL)
  2. washThe combined organic layers were washed with 1 N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b5707bd186154615b56abc97937bdba3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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