p-Toluenesulfonic acid → 2-Propenoic acid, 3-(2-hydroxy-5-methylphenyl)-, ethyl ester

HRID 655068Notes

Reaction equation

HRID 655068 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[O:14]C1CCCCO1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([O:3][C:4](=[O:21])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 539559873-[5-Methyl-2-(tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid ethyl ester

Product 1

HCID 153056922-Propenoic acid, 3-(2-hydroxy-5-methylphenyl)-, ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 193.7 g 3-[5-methyl-2-(tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid ethyl ester (Bunce, R., Moore, J., Org. Prep. Proc., 29(3), 293 (1997)) and 2 g p-toluenesulfonic acid in 2.5 l of ethanol was stirred at room temperature for 24 hours. Then the reaction mixture was concentrated and the residue was diluted with ether, washed with saturated sodium bicarbonate and brine, dried and evaporated to dryness. The resulting yellow solid was recrystallized to yield 97.7 g of colourless crystals.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. additionthe residue was diluted with ether
  3. washwashed with saturated sodium bicarbonate and brine
  4. customdried
  5. customevaporated to dryness
  6. customThe resulting yellow solid was recrystallized

Sources & evidence

ORD record
ord-f9bd66031b74495f9115760ce39e80c9
Source dataset
uspto-grants-2011_12
Patent number
USRE043006E1

Reaction notes

Loading…