Dichloromethane → HCID 20224539, compound

HRID 1381968Notes

Reaction equation

HRID 1381968 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-].[K+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)Cl>O>[C:14]1([S:20]([OH:22])(=[O:1])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH:5][C:4]1[C:6]([O:7][CH3:8])=[CH:9][CH:10]=[CH:11][C:3]=1[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 8991o-VanillinHCID 14797Potassium Hydroxide

Product 1

HCID 20224539HCID 20224539, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of o-vanillin (537.5 g, 3.54 mole) in water (3.6 L) containing potassium hydroxide (215 g, 3.77 mole) was treated with benzenesulfonyl chloride (360 mL, 2.83 mole) dropwise over a period of one hour. Methylene chloride (75 ml) was added and the mixture was stirred overnight. The resultant solid was collected by filtration and washed with 500 mL of 5% aqueous potassium hydroxide and 1 L of water. The solid was dried in vacuo at 70°-90° C. to give the title compound, 750 g, mp 115°-119° C.

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. washwashed with 500 mL of 5% aqueous potassium hydroxide and 1 L of water
  3. customThe solid was dried in vacuo at 70°-90° C.

Sources & evidence

ORD record
ord-e2b155db59394dd5b24c6a9195c36d46
Source dataset
uspto-grants-1989_02
Patent number
US04804756

Reaction notes

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