Salicyl Alcohol → Benzenemethanol, 2-butoxy- (9CI)
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH2:19][CH3:20]>C(#N)C>[CH2:17]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][OH:1])[CH2:18][CH2:19][CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-Hydroxymethyl phenol (1.2 g, 9.6 mmol) was dissolved in 10 mL of dry acetonitrile. Potassium carbonate (1.3 g, 9.6 mmol) and 1-iodobutane (1 mL, 8.8 mmol) were added and the reaction was stirred at room temperature for 3 days and at 50° C. for 1 day. The solvent was removed and the residue partitioned between ethyl acetate and 1N hydrochloric acid. The acidic aqueous layer was extracted with ethyl acetate(3×25 mL). The combined organic extracts were washed with 0.5 N sodium hydroxide (3×20 mL), dried over MgSO4, filtered and concentrated to provide the title compound (800 mg, 50% yield) as a colorless oil.
Workup
- customThe solvent was removed
- customthe residue partitioned between ethyl acetate and 1N hydrochloric acid
- extractionThe acidic aqueous layer was extracted with ethyl acetate(3×25 mL)
- washThe combined organic extracts were washed with 0.5 N sodium hydroxide (3×20 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-83402499895149f7be7343f8c6e3b96d
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07038077B2
Reaction notes
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