HCID 22039831, compound → HCID 22039039, compound

HRID 1066637Notes

Reaction equation

HRID 1066637 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-1842470cefc447e5862225f2dfee9bc2
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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