Benzenesulfonyl chloride → 2-Hydroxy-3-ethoxybenzaldehyde benzenesulphonate

HRID 654378Notes

Reaction equation

HRID 654378 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12])[CH3:2].[OH-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:15]1([S:21]([OH:23])(=[O:3])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH:12][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 68117O-Ethylvanillin

Product 1

HCID 884448222-Hydroxy-3-ethoxybenzaldehyde benzenesulphonateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

3-Ethoxysalicylaldehyde (498 g, 3 moles) and sodium hydroxide (140 g, 3.5 moles) in 1.5 liters of water are introduced into a 4 liter reactor provided with mechanical stirring, a condenser and a nitrogen inlet. The mixture is taken to 60° C. and benzenesulphonyl chloride is added dropwise over three-quarters of an hour. The mixture is heated to 75° C. for a quarter of an hour. It is cooled. An oil forms which crystallizes with time. It is filtered, washed with water and dried. The 2-hydroxy-3-ethoxybenzaldehyde benzenesulphonate (901 g, yield=98%) is used for the following stage. It can be recrystallized from 90:10 acetic acid/water. A white powder is obtained, m.p.=68°-69° C.

Workup

  1. customprovided with mechanical stirring, a condenser and a nitrogen inlet
  2. customis taken to 60° C.
  3. temperatureIt is cooled
  4. customAn oil forms which crystallizes with time
  5. filtrationIt is filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2c8013f923a7457588161d646a65a30d
Source dataset
uspto-grants-1992_07
Patent number
US05131911

Reaction notes

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