Sulfuric Acid → (RS)-2-hydroxysulphonyloxymethylindoline

HRID 262122Notes

Reaction equation

HRID 262122 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.[S:12](=O)(=[O:15])([OH:14])[OH:13]>O>[OH:15][S:12]([O:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27946642,3-dihydro-1H-indol-2-ylmethanol

Product 1

HCID 21320152(RS)-2-hydroxysulphonyloxymethylindoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

(RS)-2-Hydroxymethylindoline (29.8 g) is dissolved in a mixture of 34 N sulphuric acid (11.5 cc) and water (60 cc). The mixture is heated whilst distilling the water under reduced pressure (10 mm Hg), the heating bath being raised gradually to 160° C., which temperature is maintained for 2 hours. (RS)-2-Hydroxysulphonyloxymethylindoline (45.8 g) is thus obtained in the form of white crystals.

Workup

  1. temperatureThe mixture is heated
  2. distillationwhilst distilling the water under reduced pressure (10 mm Hg)
  3. temperaturewhich temperature is maintained for 2 hours

Sources & evidence

ORD record
ord-4ff67b2684a64eb4b537efc11e65233f
Source dataset
uspto-grants-1979_05
Patent number
US04153699

Reaction notes

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