P-Cresol → HCID 19784610, compound

HRID 1656060Notes

Reaction equation

HRID 1656060 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]1[CH:22]=[CH:21][C:15]([CH:16](O)[C:17]([OH:19])=[O:18])=[CH:14][CH:13]=1)[CH3:10]>>[CH2:9]([O:11][C:12]1[CH:22]=[CH:21][C:15]([CH:16]2[C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=3[O:19][C:17]2=[O:18])=[CH:14][CH:13]=1)[CH3:10]

Participants

3

Reactant 2

HCID 2879P-CresolHCID 18955528HCID 18955528, compound

Product 1

HCID 19784610HCID 19784610, compoundYield 76%

Procedure

A mixture of 162 g (1.50 mol) of 4-methylphenol and 196.2 g (1.0 mol) of 4-ethoxymandelic acid are stirred under nitrogen for 2 hours at 140°-150° C. Stirring is then continued for 1.5 hours at 150° C. under a slight vacuum (50 mbar). Excess 4-methoxyphenol is removed by distillation under a high vacuum. Crystallisation of the residue from xylene/ethanol yields 204 g (76%) of 3-(4-ethoxyphenyl)-5-methylbenzofuran-2-one of m.p. 82°-86° C.

Workup

  1. stirringStirring
  2. waitis then continued for 1.5 hours at 150° C. under a slight vacuum (50 mbar)
  3. customExcess 4-methoxyphenol is removed by distillation under a high vacuum
  4. customCrystallisation of the residue from xylene/ethanol

Sources & evidence

ORD record
ord-91b1afbb6abc4dc6896b84ee7ac9de05
Source dataset
uspto-grants-1993_10
Patent number
US05252643

Reaction notes

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