p-Toluenesulfonic acid → HCID 18973911, compound

HRID 2395005Notes

Reaction equation

HRID 2395005 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30]C1C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][CH3:30])=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18973920HCID 18973920, compound

Product 1

HCID 18973911HCID 18973911, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[3-(2-benzyloxy-5-hydroxymethylphenyl) propyl]benzoate (5.31 g) in methanol (100 ml) was added 4-methylbenzenesulphonic acid (3.11 g). The reaction was heated at reflux for 18 hours, the solvent evaporated, the residue dissolved in EtOAc, washed with brine and the solvent evaporated to give methyl 4-[3-(2-benzyloxy-5-methoxymethylphenyl)propyl]benzoate (3.64 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with brine
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-7cbfd6cb993845d0b6896d48a4c961e3
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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