Sodium borohydride → [4-chloro-2-(hydroxymethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

HRID 38287Notes

Reaction equation

HRID 38287 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:4]([CH:17]=[O:18])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:9])=[C:4]([CH2:17][OH:18])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 51357407Tert-butyl 2-(4-chloro-2-formylphenoxy)acetate

Product 1

HCID 86631069[4-chloro-2-(hydroxymethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl EsterYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4-chloro-2-formylphenoxy)-acetic acid, 1,1-dimethylethyl ester (2.1 g) in ethanol (20 ml) was added sodium borohydride (0.29 g). After stirring for 10 minutes the reaction was concentrated in vacuo and water added to the residue. The organics were extracted into ethylacetate, washed with brine, dried (MgSO4) and concentrated in vacuo to give the subtitle compound as an oil (2 g).

Workup

  1. concentrationwas concentrated in vacuo and water
  2. additionadded to the residue
  3. extractionThe organics were extracted into ethylacetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e1c971ff38d4c77a5661f9306b08c84
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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