Water → Tert-butyl 3-[2-(hydroxymethyl)-3-methylphenyl]propanoate

HRID 64424Notes

Reaction equation

HRID 64424 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:10]=[CH:11]/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[BH4-].[Na+].O.C(OCC)(=O)C>CO.[Ni](Cl)Cl>[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86713434HCID 86713434, compound

Product 1

HCID 86713433Tert-butyl 3-[2-(hydroxymethyl)-3-methylphenyl]propanoateYield 99.3%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 789 mg of tert-butyl (2E)-3-[2-(hydroxymethyl)-3-methylphenyl]acrylate in 16 ml of methanol was added 82 mg of nickel chloride (II). Then, 240 mg of sodium borohydride was added thereto under ice-cooling, followed by stirring for 4 hours under ice-cooling. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 790 mg of tert-butyl 3-[2-(hydroxymethyl)-3-methylphenyl]propanoate.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68420bd7c3124e1181ffe7e2d46101f5
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

Loading…