Ammonium Chloride → 2-(3-(Diethoxymethyl)phenyl)ethanol
Reaction equation
[Cl-].[NH4+].[OH:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)C=O.C(O[CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])C>CCO>[CH2:22]([O:21][CH:17]([O:18][CH2:19][CH3:20])[C:12]1[CH:13]=[C:6]([CH2:5][CH2:4][OH:3])[CH:7]=[CH:8][CH:11]=1)[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Ammonium chloride (0.08 g) was added to a solution of 3-(2-hydroxyethyl)benzaldehyde (example 20, step b) (0.45 g) and triethoxymethane (0.55 g) in EtOH (8 mL) and the reaction mixture heated at 70° C. for 3 h. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The ethyl acetate solution was dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a gum. Yield 0.24 g.
Workup
- temperatureAfter cooling
- customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution
- dry with materialThe ethyl acetate solution was dried over sodium sulphate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-66268a2e9b0548628bb48820715b8d78
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
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