Benzene → HCID 19041781, compound

HRID 1684040Notes

Reaction equation

HRID 1684040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[O:7].[CH2:13](O)[CH2:14][CH2:15][OH:16].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH:6]2[O:16][CH2:15][CH2:14][CH2:13][O:7]2)[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 104421,3-PropanediolHCID 817473,5-DimethoxybenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 19041781HCID 19041781, compound

Reagents, catalysts & solvents 1

HCID 22272175Benzene--water (1/1)Solvent

Procedure

3,5-dimethoxybenzaldehyde (5.00 g,30.12 mmole), 1,3-propanediol (9.15 g, 120.5 mmole), pyridinium para-toluenesulfonate (3.02 g, 12.05 mmole) and 80 ml dry benzene were refluxed with Dean-Stark removal of the benzene-water azeotrope for 12 hours. The benzene was removed in vacuo and the remaining oil redissolved in dichloromethane and was washed with 10% NaHCO3 and H2O. The organic layer was washed over Na2SO4 and concentrated to an oil in vacuo which was purified by flash column chromatography using 2:1 hexane/ethyl acetate containing 0.5% triethylamine as eluent. (5.731 g, 85%).

Workup

  1. customThe benzene was removed in vacuo
  2. dissolutionthe remaining oil redissolved in dichloromethane
  3. washwas washed with 10% NaHCO3 and H2O
  4. washThe organic layer was washed over Na2SO4
  5. concentrationconcentrated to an oil in vacuo which
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-a7aa6023c03746d38a32500e66e1c0a6
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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