Citric Acid → Phenol, 5-iodo-2-(1-methylethoxy)-

HRID 1438096Notes

Reaction equation

HRID 1438096 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:6]=1[O:12][CH:13]([CH3:15])[CH3:14])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)C>CO.C1COCC1.[Li+].[OH-]>[I:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH:13]([CH3:15])[CH3:14])=[C:5]([OH:4])[CH:10]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 587891455-Iodo-2-isopropoxyphenyl acetate

Product 1

HCID 58788960Phenol, 5-iodo-2-(1-methylethoxy)-Yield 82.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-2-isopropoxyphenyl acetate (10 mmol) in MeOH (5 mL) and THF (15 mL), LiOH (1.0 M, 15 mL) was added at 0° C. After the mixture was stirred at rt for 3.0 h, 5% citric acid (30 mL) and diethyl ether (150 mL) was added. The organic extract was washed with brine, dried over Na2SO4 and evaporated to give 5-iodo-2-isopropoxyphenol (2.3 g) as an oil.

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-66f57bcf9143460a907071c6805b1da7
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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