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

HRID 553259Notes

Reaction equation

HRID 553259 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-bd80bf81e0d64643b078840efe4bcf2e
Source dataset
uspto-grants-2011_05
Patent number
US07951971B1

Reaction notes

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