Water → HCID 69891053, compound

HRID 2307900Notes

Reaction equation

HRID 2307900 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](OC)[CH:3]=1.[C:11]1([CH2:17][C:18]([OH:20])=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:21](N(CC)CC)C.[OH2:28]>C(OC(=O)C)(=O)C>[C:11]1([C:17]2[C:18]([O:20][CH3:21])=[CH:7][CH:6]=[CH:5][C:4]=2[CH:3]=[CH:2][C:1]([OH:10])=[O:28])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 115693-Methoxybenzaldehyde

Product 1

HCID 69891053HCID 69891053, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of m-anisaldehyde (29.37 g, 21.57 mmol) and phenylacetic acid (29.37 g, 21.57 mmol) in acetic anhydride (200 mL) was stirred with triethylamine (30 mL). The reaction mixture was heated at reflux for 4 hours, then cooled to 80-90° C., then water (500 mL) was added slowly. An oil separated, which upon stirring and cooling produced a light orange solid. The solid was filtered, washed with water and dried to afford the desired product (35 g, 64% yield). NMR was consistent with the structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customAn oil separated
  4. temperaturecooling
  5. customproduced a light orange solid
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-c2ab9e4145324c85b09d35005c7a2e97
Source dataset
uspto-grants-2004_12
Patent number
US06833366B1

Reaction notes

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