Ethanol → HCID 54247629, compound

HRID 462530Notes

Reaction equation

HRID 462530 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-d5ecec48c7e845f78b49f3d4472f97e3
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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