Hydrochloric Acid → 4-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate

HRID 27633Notes

Reaction equation

HRID 27633 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:14])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3].[OH-].[Na+].[BH4-].[Na+].Cl>O.CO>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([OH:13])=[C:10]([C:11]([CH3:16])([CH3:15])[CH2:12][OH:14])[CH:17]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonateHCID 4311764Sodium borohydride

Product 1

HCID 233412804-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonateYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2,3-Dihydro-2-hydroxy-3,3-dimethylbenzofuran-5-yl methane sulphonate (129 parts) was added to a solution of sodium hydroxide (120 parts) in water (1200 parts) and methanol (320 parts). Sodium borohydride (19 parts) was added portionwise with vigorous stirring at 15°-20° C. The mixture was stirred for three hours, then acidified with hydrochloric acid and filtered to give 4-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate (117 parts, 90% yield). Recrystallisation from 1,2-dichloroethane gave the pure product, melting point 122°-124° C.

Workup

  1. stirringThe mixture was stirred for three hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-09d560dda3a94843bf575787c4f34d7b
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Reaction notes

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