Methanol → Methyl (4-cyanophenyl)acetate

HRID 2172679Notes

Reaction equation

HRID 2172679 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)#[N:6].[CH3:17]O>>[CH3:17][O:15][C:14](=[O:16])[CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]#[N:6])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 795874-Cyanophenylacetic acid

Product 1

HCID 1512619Methyl (4-cyanophenyl)acetate

Procedure

Thionyl chloride (1.1 mL, 15.07 mmol) was added to cool MeOH (70 mL) at 0° C. After 5 min 2-(4-cyanophenyl)acetic acid (1 g, 6.21 mmol) was added. After 30 min, cooling was removed and the mixture stirred for 21 h at RT. The solvent was removed and toluene was added and evaporated 3 times to give a sticky yellow solid. The product was used crude for the next step.

Workup

  1. temperaturecooling
  2. customwas removed
  3. customThe solvent was removed
  4. additiontoluene was added
  5. customevaporated 3 times
  6. customto give a sticky yellow solid

Sources & evidence

ORD record
ord-76d8b576a98c4997a9027a2637a3f33d
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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