HCID 22039831, compound → HCID 22039039, compound

HRID 1016804Notes

Reaction equation

HRID 1016804 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-d36ac77589414117914a966597c91302
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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