Hydrochloric Acid → (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonate

HRID 963985

Reaction equation

HRID 963985 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.[O:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH:13]1[CH2:22][OH:23].Cl>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][CH:13]2[O:12][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 193141,4-Benzodioxane-2-methanol

Product 1

HCID 4522296(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonateYield 85.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of toluene-4-sulphonyl chloride (60.25 g) in pyridine (75 ml) was added dropwise at 20° C. to a stirred solution of 1-(1,4-benzodioxan-2-yl)methanol (50 g) in pyridine (100 ml) and the mixture was stirred at ambient temperature for 18 hours then poured onto an excess of ice and hydrochloric acid (5M). The resulting solid was collected by filtration, washed well with water and dried in vacuo to give 1,4-benzodioxan-2-ylmethyl toluene-4-sulphonate as an off-white solid (82.3 g), m.p. 75°-78° C.

Workup

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

Sources & evidence

ORD record
ord-453116f7021248a1b98c6a004141c30e
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Linked notes

Loading…