Benzene → HCID 86750973, compound

HRID 1684030Notes

Reaction equation

HRID 1684030 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]([SH:15])[CH2:13][SH:14])[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:27][CH3:28])[C:25]=1[OH:26])[CH:21]=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:28][O:27][C:24]1[CH:23]=[C:20]([C@H:21]2[S:15][C@H:12]([C:5]3[CH:6]=[C:7]([O:10][CH3:11])[C:8]([OH:9])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:13][S:14]2)[CH:19]=[C:18]([O:17][CH3:16])[C:25]=1[OH:26]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8655SyringaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19041797HCID 19041797, compound

Product 1

HCID 86750973HCID 86750973, compound

Reagents, catalysts & solvents 1

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

Procedure

1-(3,5-dimethoxy-4-hydroxyphenyl-1,2-ethanedithiol (40) (2.46 g, 10.0 mmole), 3,5-dimethoxy-4-hydroxybenzaldehyde (indicated as arylaldehyde E in FIG. 1) (1.32 g, 7.20 mmole) and 1.00 g of pyridinium paratoluene sulfonate are added to 50 ml dry benzene and refluxed with Dean-Stark removal of the benzene-water azeotrope overnight. The benzene is removed in vacuo, and the remaining oil redissolved in dichloromethane. The organic layer is washed with 10% NaHCO3 and H2O. The organic layer is dried over MgSO4, filtered, and evaporated in vacuo to a white solid which is recrystallized from methanol (2.510 g, 85%). The trans isomer (0.683 g) is isolated by recrystallization from methanol. NMR: (CDCl3) 3.45,dd,1H;3.61,dd,1H; 3.91,s,6H;3.92,s,6H;5.07,dd,1H;5.50,d,2H;5.83,s,1H; 6.73,s,2H;6.84,s,2H. M.S.: (CI) 411 (100%). Melting Point: 169°-170° C. C,H,S Analysis: (theoretical, actual) C (55.59,55.58); H (5.40,5.44); S (15.62,15.56).

Workup

  1. customThe benzene is removed in vacuo
  2. dissolutionthe remaining oil redissolved in dichloromethane
  3. washThe organic layer is washed with 10% NaHCO3 and H2O
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo to a white solid which
  7. customis recrystallized from methanol (2.510 g, 85%)
  8. customThe trans isomer (0.683 g) is isolated by recrystallization from methanol

Sources & evidence

ORD record
ord-195fa82b63ee4f46bc620b376fec09f6
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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