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

HRID 1960169Notes

Reaction equation

HRID 1960169 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH3:11][Li].Cl>O1CCCC1>[CH3:9][C:8]([CH3:11])([OH:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 83752'-HydroxyacetophenoneHCID 178418348HCID 178418348, compound

Product 1

HCID 8279552-(2-Hydroxypropan-2-yl)phenolYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated.

Workup

  1. additionwas added dropwise over 30 minutes
  2. customThe layers were separated
  3. washThe organic phase was washed with 30 ml of brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff5b466581a647e5a08de45c8589ea51
Source dataset
uspto-grants-2013_04
Patent number
US08410309B2

Reaction notes

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