Benzoyl chloride → 5-Formyl-2-methoxyphenyl benzoate

HRID 1489696Notes

Reaction equation

HRID 1489696 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[OH-].[Na+].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:14]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 12127IsovanillinHCID 14798Sodium Hydroxide

Product 1

HCID 9581385-Formyl-2-methoxyphenyl benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred suspension of 3-hydroxy-4-methoxybenzaldehyde (50 g) in water (200 mL) at between 0° and 5° C. is treated dropwise with an aqueous solution of sodium hydroxide (200 mL; 20% w/v), followed at between 0° and 5° C. by benzoyl chloride (38 mL). The reaction mixture is stirred at between 0° and 5° C. for 1 hour and then it is allowed to warm to room temperature and is stirred for a further period of 2 hours. The resulting solution is extracted with dichloromethane (2×200 mL) and the combined extract is washed with water (200 mL), dried over magnesium sulfate and concentrated, to give 2-methoxy-5-formylphenyl benzoate (35.2 g), m.p. 70°-72° C.

Workup

  1. stirringis stirred for a further period of 2 hours
  2. extractionThe resulting solution is extracted with dichloromethane (2×200 mL)
  3. extractionthe combined extract
  4. washis washed with water (200 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bbcbc65365d64fdbb53d9f9dc277814b
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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