p-Toluenesulfonic acid → HCID 5194456, compound

HRID 2292402Notes

Reaction equation

HRID 2292402 reaction equation
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[O:10][CH2:9][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][O:8]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 707414-BromobenzaldehydeHCID 1175092-Pentyl-1,3-propanediolHCID 516892Sodium Bicarbonate

Product 1

HCID 5194456HCID 5194456, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of compound from Example 6 (31 g, 0.21 mol), 4-bromobenzaldehyde (38.8 g, 0.21 mol) and 4-toluenesulphonic acid (110 mg) in dry toluene (200 cm3) was heated under reflux (3 h) using a Dean and Stark apparatus. On cooling to room temperature the mixture was poured into aqueous sodium hydrogen carbonate solution (5%, 70 cm3) and the separated organic layer washed with aqueous sodium hydrogen carbonate solution (5%, 2×60 cm3), water (2×60 cm3) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by crystalliation from methanol to remove the cis-isomer.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux (3 h)
  3. washthe separated organic layer washed with aqueous sodium hydrogen carbonate solution (5%, 2×60 cm3), water (2×60 cm3)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by crystalliation from methanol
  7. customto remove the cis-isomer

Sources & evidence

ORD record
ord-90b67ebd837a4db6b886ad009be59692
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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