Potassium Hydroxide → Phenol, 2,3,5-trimethyl-4-(phenylmethoxy)-

HRID 374294Notes

Reaction equation

HRID 374294 reaction equation
[OH-].[K+].CC(C)(C)C([O:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([CH3:23])[C:9]=1[CH3:24])=O>O.CO.C1(C)C=CC=CC=1>[CH3:24][C:9]1[C:10]([CH3:23])=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH3:14])=[CH:13][C:8]=1[OH:7]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 230757052,2-Dimethylpropanoic acid, 2,3,5-trimethyl-4-(phenylmethoxy)phenyl ester

Product 1

HCID 4303797Phenol, 2,3,5-trimethyl-4-(phenylmethoxy)-Yield 71.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 20.8 g (2.1×177 mmol) of potassium hydroxide in 100 mL of water is added to a solution of 57.8 g (177 mmol) of 2,2-dimethylpropanoic acid, 2,3,5-trimethyl-4-(phenylmethoxy)phenyl ester (Example B) in 300 mL of methanol. The solution is stirred at reflux for 6 hours, then permitted to stir at ambient temperature for another 8 hours. The solvent is removed on a rotary evaporator and the residual aqueous solution (dark brown) is diluted with 100 mL of water and acidified with excess 6N hydrochloric acid solution (40 mL). The product is isolated with diethyl ether and the diethyl ether solution is washed with 2×100 mL saturated (10%) sodium bicarbonate solution, brine, dried (magnesium sulfate) and evaporated leaving 48.4 g of crude product as a light brown solid. Chromatography on a 6.5 cm column containing 350 g of silica gel prepared in toluene and elution with 95% toluene:5% ethyl acetate affords 30.6 g of the title compound; mp 101°-103° C.

Workup

  1. temperatureat reflux for 6 hours
  2. stirringto stir at ambient temperature for another 8 hours
  3. customThe solvent is removed on a rotary evaporator
  4. additionthe residual aqueous solution (dark brown) is diluted with 100 mL of water
  5. customThe product is isolated with diethyl ether
  6. washthe diethyl ether solution is washed with 2×100 mL saturated (10%) sodium bicarbonate solution, brine
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated
  9. customleaving 48.4 g of crude product as a light brown solid
  10. additionChromatography on a 6.5 cm column containing 350 g of silica gel
  11. washelution with 95% toluene

Sources & evidence

ORD record
ord-24ad1b18c61f4b50a861f1e539ae82a4
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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