2-[(2-Methyl-2-oxiranyl)methyl]phenol → (2-Methyl-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 648221Notes

Reaction equation

HRID 648221 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1([CH3:12])[O:11][CH2:10]1>C(Cl)Cl>[OH:11][CH2:10][C:9]1([CH3:12])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1]1

Participants

3

Reactant 1

HCID 118160462-[(2-Methyl-2-oxiranyl)methyl]phenol

Product 1

HCID 20482667(2-Methyl-2,3-dihydro-1-benzofuran-2-yl)methanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-hydroxyphenyl)-2-methyl-2,3-epoxypropane (52.7 g) and silica (Kieselgel 60; 70-230 mesh) (150 g) in methylene chloride (300 ml) was stirred at room temperature for 24 hours. Removal of the solvent gave a residue of silica and absorbed product and this mixture was stirred with ethyl acetate for 3 hours. After filtration the ethyl acetate filtrate was dried and the solvent evaporated in vacuo to give the desired alcohol 49.6 g. This crude product was dissolved in methylene chloride and washed with 1 N aqueous sodium hydroxide solution, water and then dried. Removal of the solvent gave the alcohol as a yellow oil 37 g; I.R. νmax 3700-3200 cms-1.

Workup

  1. customRemoval of the solvent
  2. customgave a residue of silica
  3. customabsorbed product
  4. stirringthis mixture was stirred with ethyl acetate for 3 hours
  5. filtrationAfter filtration the ethyl acetate filtrate
  6. customwas dried
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-34915629bf874e3488235eca6d307e01
Source dataset
uspto-grants-1983_10
Patent number
US04411908

Reaction notes

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