Reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].Br[CH2:15][CH2:16][CH:17]1[O:22][CH2:21][CH2:20][CH2:19][O:18]1>O.C(OCC)(=O)C.C(O)(=O)C>[C:3]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:15][CH2:16][CH:17]1[O:22][CH2:21][CH2:20][CH2:19][O:18]1)([CH3:6])([CH3:4])[CH3:5]Participants
Procedure
Sodium hydroxide (3.46 g, 1.3 eq) was taken up in water (20 mL) and stirred for about 30 minutes. Then 3-tert-butyl phenol (10.0 g, 66.6 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. Next, 2-(2-bromoethyl)-[1,3]dioxane (9.9 mL, 1.1 eq) was added ant the resulting mixture was heated at reflux for 40 hours. The reaction mixture was cooled to room temperature and then added ethyl acetate (150 mL) and with stirring acetic acid was added to pH=4, followed by dilution with water (100 mL) and ethyl acetate (150 mL). After partitioning, the layers were separated and then washed the organic layer with water (3×100 mL) and the ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (16.91 g).
Workup
- stirringthe resulting mixture was stirred at room temperature for 30 minutes
- temperaturewas heated
- temperatureat reflux for 40 hours
- customAfter partitioning
- customthe layers were separated
- washwashed the organic layer with water (3×100 mL)
- dry with materialthe ethyl acetate layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-83be275999f24c53aa4056ecd01cbb9e
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318719B2
Linked notes
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