Sulfuric Acid → HCID 54239901, compound

HRID 461817Notes

Reaction equation

HRID 461817 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1.[S:13](=O)(=[O:16])([OH:15])[OH:14]>O>[OH:16][S:13]([O:1][CH2:2][C@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 723422[(3R)-1,2,3,4-Tetrahydroisoquinolin-3-yl]methanol

Product 1

HCID 54239901HCID 54239901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (R)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (22.8 g.) in a mixture of sulphuric acid (d = 1.83; 7.9 cc.) and water (50 cc.) is concentrated for 1 hour at 100° C., under reduced pressure (20 mm.Hg) and then for 1 hour at 160° C. The residue crystallises on cooling. (R)-3-Hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (33.9 g.) is thus obtained in the form of a white crystalline mass melting at 318° C.

Workup

  1. concentrationis concentrated for 1 hour at 100° C., under reduced pressure (20 mm.Hg)
  2. customThe residue crystallises
  3. temperatureon cooling

Sources & evidence

ORD record
ord-436d7d8121e44fa28f91acc93e7b6f1a
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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