Acetic Acid → 2-(2-Hydroxypropan-2-yl)phenol

HRID 512919Notes

Reaction equation

HRID 512919 reaction equation
C[Mg]Cl.OC[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O.[C:14]([OH:17])(=O)[CH3:15].C1C[O:21]CC1>ClCCl>[OH:21][C:8]([C:13]1[CH:12]=[CH:11][CH:10]=[CH:15][C:14]=1[OH:17])([CH3:9])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 68490alpha-HydroxyacetophenoneHCID 178418332HCID 178418332, compound

Product 1

HCID 8279552-(2-Hydroxypropan-2-yl)phenolYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl magnesium chloride (134 ml, 3M in THF) kept under nitrogen, at 0° C. was added a solution of 2-hydroxy acetophenone (50 g, 367 mmol) in anhydrous THF (100 ml). The reaction mixture was stirred. After completion of the reaction, the reaction mixture was treated with 4M acetic acid (500 ml) followed by usual workup in dichloromethane and FC to give hydroxy phenol 31 (25 g, 45%) as a colorless oil.

Workup

  1. customkept under nitrogen, at 0° C.
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-76c1fd76f1a84fa0a3dc8155ccb03f02
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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