Benzenesulfonyl chloride → 2-Formyl-6-methoxyphenyl benzenesulfonate

HRID 652592Notes

Reaction equation

HRID 652592 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:14]1([S:20]([O:5][C:4]2[C:6]([O:7][CH3:8])=[CH:9][CH:10]=[CH:11][C:3]=2[CH:2]=[O:1])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8991o-VanillinHCID 14798Sodium Hydroxide

Product 1

HCID 2337652-Formyl-6-methoxyphenyl benzenesulfonateYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

o-Vanillin (350 g, 2.3 mols) was added to a solution of NaOH (166 g, 4.15 mols) in 2 l water. Benzenesulfonyl chloride (485 g, 2.74 mols) was added to the slurry at 20°-25° C. over 1 hour. The solid which formed was collected on a filter, washed with 2 l water, and redissolved in CH2Cl2. That solution was dried (MgSO4) and evaporated to a slurry. The solid was collected on a filter, the filtrate was further evaporated and filtered. The solid was washed with MeOH and dried in vacuo to afford the desired product, (511 g, 81.4%), mp 120°-122° C.

Workup

  1. customThe solid which formed
  2. customwas collected on a filter
  3. washwashed with 2 l water
  4. dissolutionredissolved in CH2Cl2
  5. dry with materialThat solution was dried (MgSO4)
  6. customevaporated to a slurry
  7. customThe solid was collected on a filter
  8. customthe filtrate was further evaporated
  9. filtrationfiltered
  10. washThe solid was washed with MeOH
  11. customdried in vacuo

Sources & evidence

ORD record
ord-e99e9095bfe44ccdbd3965e13ac09b0d
Source dataset
uspto-grants-1987_06
Patent number
US04672116

Reaction notes

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