Benzene → HCID 19041763, compound

HRID 1684038Notes

Reaction equation

HRID 1684038 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([I:13])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[CH2:14](O)[CH2:15][CH2:16][OH:17].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[O:17][CH2:16][CH2:15][CH2:14][O:7]2)[CH:8]=[C:9]([I:13])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 241BenzeneHCID 104421,3-PropanediolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27781133-Iodo-4,5-dimethoxybenzaldehyde

Product 1

HCID 19041763HCID 19041763, compound

Reagents, catalysts & solvents 1

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

Procedure

3,4-dimethoxy-5-iodobenzaldehyde (41) (FIG. 22) (5.814 g,19.9 mmole), 1,3-propanediol (6.13 g, 79.6 mmole), pyridinium para-toluenesulfonate (2.0 g, 7.96 mmole) and 100 ml dry benzene were refluxed with Dean-Stark removal of the benzene-water azeotrope overnight. The benzene was removed in vacuo and the remaining oil redissolved in diethyl ether and was washed with 10% NaHCO3 and H2O. The organic layer was washed over MgSO4, and concentrated to a white solid in vacuo. (6.823 g, 98%). The solid can be recrystallized from hexane/ethyl acetate.

Workup

  1. customThe benzene was removed in vacuo
  2. dissolutionthe remaining oil redissolved in diethyl ether
  3. washwas washed with 10% NaHCO3 and H2O
  4. washThe organic layer was washed over MgSO4
  5. concentrationconcentrated to a white solid in vacuo
  6. customThe solid can be recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-cb837c098b784ba3ae9d4d17364d34f5
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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