P-Cresol → 3-[4-(2-Hydroxyethoxy)phenyl]-5-methylbenzofuran-2-one

HRID 22497

Reaction equation

HRID 22497 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9](O)[C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1.[CH:16]1[C:21](O)=[CH:20][CH:19]=[C:18]([CH3:23])[CH:17]=1>O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]2[C:16]3[CH:17]=[C:18]([CH3:23])[CH:19]=[CH:20][C:21]=3[O:12][C:10]2=[O:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2879P-CresolHCID 199304444-(2-Hydroxyethoxy)mandelic acid2×

Product 1

HCID 199304463-[4-(2-Hydroxyethoxy)phenyl]-5-methylbenzofuran-2-oneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 8.5 g (40.0 mmol) of 4-(2-hydroxyethoxy)mandelic acid (compound (201), Example 10, Table 2) and 12.0 g (110 mmol) of p-cresol is maintained at 180° C. under a nitrogen atmosphere for 75 minutes, during which the water formed distils off. Excess p-cresol is then distilled off in a vacuum rotary evaporator. Chromatography of the residue on silica gel using the eluent system 9:1 dichloromethane/ethyl acetate gives 6.6 g (58%) of 3-[4-(2-hydroxyethoxy)phenyl]-5-methylbenzofuran-2-one, a yellowish resin (compound (119), Table 1).

Workup

  1. customformed
  2. customdistils off
  3. distillationExcess p-cresol is then distilled off in a vacuum rotary evaporator

Sources & evidence

ORD record
ord-b6ee0b0ac5b8478abd53a04ef724aadf
Source dataset
uspto-grants-1995_06
Patent number
US05428162

Linked notes

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