Hydrochloric Acid → 8-Methoxy-1,4-benzodioxan-2-ylmethyl toluene-4-sulphonate

HRID 963990Notes

Reaction equation

HRID 963990 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[C:19]2[O:20][CH:21]([CH2:24][OH:25])[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1.Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:25][CH2:24][CH:21]2[O:20][C:19]3[C:14]([O:13][CH3:12])=[CH:15][CH:16]=[CH:17][C:18]=3[O:23][CH2:22]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 104881082-Hydroxymethyl-8-methoxy-1,4-benzodioxan

Product 1

HCID 104980328-Methoxy-1,4-benzodioxan-2-ylmethyl toluene-4-sulphonateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of toluene-4-sulphonyl chloride (5.84 g) in pyridine (10 ml) was added dropwise at 10°-15° C. to a solution of 1-(8-methoxy-1,4-benzodioxan-2-yl)methanol (5.0 g) in pyridine (30 ml) and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured onto an excess of ice and dilute hydrochloric acid. The resulting solid was collected by filtration, washed with water and dried in vacuo to yield 8-methoxy-1,4-benzodioxan-2-ylmethyl toluene-4-sulphonate as a white solid (6.61 g), m.p. 66°-68° C.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ba43c75e61bb4a9b889e9224940d8a0d
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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