HCID 22039831, compound → HCID 22039039, compound

HRID 1841768Notes

Reaction equation

HRID 1841768 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([O:10]COC)=[C:6]([CH2:14][CH3:15])[CH:5]=2)[CH2:3][CH2:2]1>C(O)(=O)C>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:14][CH3:15])[CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 22039831HCID 22039831, compound

Product 1

HCID 22039039HCID 22039039, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 12.0 g of 4-cyclopropyl-2-ethyl-1-methoxymethoxy-benzene in 240 ml of 2N acetic acid was stirred for 24 hours at 90° C. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phases were washed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed over silica gel and gave 8.7 g of 4-cyclopropyl-2-ethyl-phenol; MS (EI) m/z 162 (M), 147 (M−CH3).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phases were washed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-fb36dde8663e4ab6b4ce849287ec6cca
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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