4-(Methoxymethyl)phenylacetic acid → 4-(Methoxymethyl)phenethyl alcohol

HRID 987138Notes

Reaction equation

HRID 987138 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=[O:12])=[CH:6][CH:5]=1>C1COCC1>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 229884284-(Methoxymethyl)phenylacetic acid

Product 1

HCID 229884104-(Methoxymethyl)phenethyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(Methoxymethyl)phenyl]acetic acid (3.6 g, 20 mmole) was dissolved in THF (100 ml) and cooled on an ice-bath. BH3xTBT (1M, 40 ml, 40 mmole) was added. The reaction mixture was stirred for 6 h and then quenched with HCl (1M, 80 ml) and water (˜100 ml). THF was evaporated and the residue extracted with dicloromethane and ethyl acetate. The phases were separated and the organic phase was washed with HCl (0.3M, 100 ml and dried with Na2SO4. Evaporation gave 3.31 g, 99.6%, of the desired product.

Workup

  1. temperaturecooled on an ice-bath
  2. additionBH3xTBT (1M, 40 ml, 40 mmole) was added
  3. customquenched with HCl (1M, 80 ml) and water (˜100 ml)
  4. customTHF was evaporated
  5. extractionthe residue extracted with dicloromethane and ethyl acetate
  6. customThe phases were separated
  7. washthe organic phase was washed with HCl (0.3M, 100 ml
  8. dry with materialdried with Na2SO4
  9. customEvaporation
  10. customgave 3.31 g, 99.6%

Sources & evidence

ORD record
ord-262666dd1bb746ca95bbdc7b0b0d11e7
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

Loading…