Potassium Iodide → Veratrole

HRID 2081762Notes

Reaction equation

HRID 2081762 reaction equation
ClC1C=CC(CP(=O)(OCC)OCC)=CC=1.[CH2:17]([O:20][C:21]1[CH:28]=[CH:27][C:24](C=O)=[CH:23][C:22]=1[O:29][CH3:30])C=C.CC([O-])(C)C.[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+]>C1(OC)C=CC=CC=1>[C:22]1([O:29][CH3:30])[C:21](=[CH:28][CH:27]=[CH:24][CH:23]=1)[O:20][CH3:17]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 2855718-Crown-6HCID 99240Diethyl 4-chlorobenzylphosphonateHCID 20638234-(allyloxy)-3-methoxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 7043VeratroleYield 73%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent2×

Procedure

A solution containing 147.0 g (306 mmol) of the tetraethyl stilbene-4,4'-bis(methylenephosphonate) described in (c) above and 129.4 g (673 mmol) of the 4-allyloxy-3-methoxybenzaldehyde described in Example 2 (b) above in 900 ml of anisole, is added dropwise with stirring and at a temperature of 0° to 10° C. to a suspension containing 94.4 g (841 mmol) of potassium tert-butylate, 6.1 g (23 mmol) of 18-crown-6 and 1.75 g (10 mmol) of potassium iodide in 1300 ml of anisole. The mixture is then stirred at room temperature for an additional 1 hour and then at 110° C. for an additional 3 hours. The mixture is cooled to room temperature and the resultant solid is filtered off with suction and recrystallized first from dimethyl sulfoxide and then from veratrol (1,2-dimethoxybenzene), giving 119.5 g of yellow crystals, which corresponds to a yield of 73%.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is then stirred at room temperature for an additional 1 hour
  3. filtrationthe resultant solid is filtered off with suction
  4. customrecrystallized first from dimethyl sulfoxide

Sources & evidence

ORD record
ord-b99b0d18ca5f4c5ba697f0001fd2aaaa
Source dataset
uspto-grants-1993_02
Patent number
US05185419

Reaction notes

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