Sodium borohydride → HCID 21549130, compound

HRID 1605117Notes

Reaction equation

HRID 1605117 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)(=[O:6])[CH2:4][CH3:5]>CO>[OH:6][CH:3]([C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]([CH3:17])([CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21549187HCID 21549187, compound

Product 1

HCID 21549130HCID 21549130, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (10.6 g., 0.279 mole) was added to a stirred solution of 114.5 g. (0.458 mole) of methyl 2-(p-propionylphenoxy)-2-methylpropionate in 500 ml. of methanol, held at 5°C. in an ice bath. After the exothermic reaction had slowed, the ice bath was removed and the reaction mixture stirred for one hour at room temperature. The solvent was removed in vacuo, and the residue partitioned between ether and water containing acetic acid in slight excess of that needed to make the aqueous layer acidic. The ether layer was separated, washed with sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated in vacuo. There was thus obtained 113 g. of methyl 2-[p-(1-hydroxypropyl)phenoxy]-2-methylpropionate as a pale straw-colored oil.

Workup

  1. customAfter the exothermic reaction
  2. customthe ice bath was removed
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ether and water
  5. additioncontaining acetic acid in slight excess of
  6. customThe ether layer was separated
  7. washwashed with sodium bicarbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-235cd14d7222482fb16cc275094089c2
Source dataset
uspto-grants-1976_04
Patent number
US03948973

Reaction notes

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