2-Allylphenol → (2,3-Dihydro-1-benzofuran-2-yl)methanol

HRID 1866536Notes

Reaction equation

HRID 1866536 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])[CH:13]=[CH2:14]>ClCCl>[O:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:12][CH:13]1[CH2:14][OH:9]

Participants

4

Reactant 2

HCID 156242-AllylphenolHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 2795428(2,3-Dihydro-1-benzofuran-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of meta-chloroperbenzoic acid (96.4 g, 335 mmol) in dichloromethane (500 mL) was added to an ice-cold solution of 2-allylphenol (30 g, 224 mmol) in dichloromethane (1 L) and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 18 hours. The reaction mixture was then re-cooled to 0° C., quenched with 2M sodium hydroxide solution (700 mL) and stirred for 30 minutes. The organic layer was then separated, dried over magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil was purified by HPLC using a Chiralpak AD 250*4.6 mm column and hexane:isopropanol (90:10) as the eluant, to afford the title compound.

Workup

  1. temperatureThe reaction mixture was then re-cooled to 0° C.
  2. customquenched with 2M sodium hydroxide solution (700 mL)
  3. stirringstirred for 30 minutes
  4. customThe organic layer was then separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe oil was purified by HPLC

Sources & evidence

ORD record
ord-49756e99fdd749579bf3a5d77355d41a
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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