HCID 22039831, compound → HCID 22039039, compound

HRID 1790596Notes

Reaction equation

HRID 1790596 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-4f91d52ba0f449b693806997400023fa
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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