Water → HCID 24754683, compound

HRID 1028927Notes

Reaction equation

HRID 1028927 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH:14]=[O:15])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[BH4-].[Na+].O>CO>[C:1]1([CH3:21])[CH:2]=[CH:3][C:4]([S:7]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:14][OH:15])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1714278HCID 1714278, compoundHCID 4311764Sodium borohydride

Product 1

HCID 24754683HCID 24754683, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
17.5 °C

Procedure

To a cooled solution of 3-[(p-Toluenesulfonyl)oxy]-4-methoxybenzaldehyde 21 (9.0 g, 29 mmol) in methanol (25 mL) was added sodium borohydride (0.55 g, 14.5 mmol) in methanol (2.5 mL) over a period of 5-10 min maintaining the temperature around 15-20° C. The reaction mixture was maintained at that temperature for further 30 min and checked TLC for completion of the reaction. Water was added to the reaction mixture and the solid formed was filtered, washed with water and dried to afford 22. Yield: 97%; white solid mp 88-90° C. 1H NMR: δ 2.41 (s, 3H, CH3), 3.59 (s, 3H, OCH3), 4.57 (s, 2H, CH2), 6.80-7.79 (m, 7H, Ar—H). Anal. Calcd for C15H16O5S: C, 58.43, H, 5.23. Found: C, 58.49, H, 5.19.

Workup

  1. temperatureThe reaction mixture was maintained at that temperature for further 30 min
  2. customfor completion of the reaction
  3. customthe solid formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ea5739a6eb5143bfb11482522707f08d
Source dataset
uspto-grants-2014_05
Patent number
US08735620B2

Reaction notes

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