Methanol → HCID 22036442, compound

HRID 1789712Notes

Reaction equation

HRID 1789712 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].[CH3:24][OH:25]>>[CH3:24][O:25][CH:19]([O:20][CH3:1])[C:18]1[CH:17]=[C:16]([CH:23]=[CH:22][CH:21]=1)[O:15][CH2:14][CH2:13][OH:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acid2×HCID 6453965Benzaldehyde, 3-(2-hydroxyethoxy)-

Product 1

HCID 22036442HCID 22036442, compound

Procedure

p-TsOH (165 mg, 0.87 mmol) was added to a solution of the product obtained in Step 1 (1.45 g, 8.73 mmol) in dry MeOH (60 mL). After being stirred for 23 h at room temperature, more p-TsOH (170 mg, 0.89 mmol) was added. After additional 4 h of stirring, the reaction was quenched by the addition of NaHCO3 (saturated aqueous solution, 70 mL) and H2O (50 mL). The aqueous phase was extracted with EtOAc (3×100 mL). The combined organic phases were washed with brine and dried (MgSO4). Evaporation of the solvents afforded a yellow oil that was used in the next step without purification. Yield 1.59 g (86%). The product contained about 5% of starting material (1H NMR).

Workup

  1. stirringAfter additional 4 h of stirring
  2. customthe reaction was quenched by the addition of NaHCO3 (saturated aqueous solution, 70 mL) and H2O (50 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvents
  7. customafforded a yellow oil that
  8. customwas used in the next step without purification

Sources & evidence

ORD record
ord-c267f725b5b74ac69532be19c367e0e2
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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