Ethanol → HCID 54247629, compound

HRID 414522Notes

Reaction equation

HRID 414522 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([C:11](=[O:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[O:18][CH2:19][CH3:20].C(O)C.[BH4-].[Na+].[OH-].[Na+]>O>[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH:11]([OH:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[O:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21280947HCID 21280947, compound

Product 1

HCID 54247629HCID 54247629, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 26 g. of 4'-amino-3',5'-diethoxy-2-(methylsulfonyl)-acetophenone in 350 ml. of ethanol and 350 ml. of water was treated with a solution of 7.0 g. of sodium borohydride in 90 ml. of water. There was also added 0.5 g. of sodium hydroxide. The mixture was stirred for 17 hours at room temperature, cooled with ice, diluted with 500 ml. of water and filtered under vacuum. After recrystallization from methanol, there was obtained 4-amino-3,5-diethoxy-α-[(methylsulfonyl)-methyl]-benzyl alcohol having a melting point of 166°-168° C.

Workup

  1. additionA suspension of 26 g
  2. temperaturecooled with ice
  3. additiondiluted with 500 ml
  4. filtrationof water and filtered under vacuum
  5. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-90f3d3a7de3c49a6a63e0516ee7975e8
Source dataset
uspto-grants-1988_12
Patent number
US04792557

Reaction notes

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