Phenol → 8-Phenoxy-1,4-dioxaspiro[4.5]decane
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[O:11]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Procedure
Step 1 A solution of 1,4-dioxaspiro[4.5]decan-8-ol (1.00 g, 6.32 mmol), phenol (0.714 g, 7.59 mmol) and triphenylphosphine (1.824 g, 6.95 mmol) in DCM (21.07 mL) was treated with diisopropyl azodicarboxylate (1.48 mL, 7.59 mmol) and the mixture was stirred at rt for 5 days. The mixture was concentrated and the residue was purified by column chromatography, eluting with a gradient from hexane to 80:20 hexane-EtOAc). The crude product was dissolved in EtOAc and the solution was washed twice with 1 M aqueous sodium hydroxide and brine, dried and concentrated to provide 8-phenoxy-1,4-dioxaspiro[4.5]decane as a colorless liquid (0.468 g, 32%). 1H NMR (500 MHz, chloroform-d) δ 7.16-7.24 (2 H, m), 6.81-6.89 (3 H, m), 4.30-4.38 (1 H, m), 3.85-3.93 (4 H, m), 1.80-1.90 (6 H, m), 1.50-1.59 (2 H, m).
Workup
- concentrationThe mixture was concentrated
- customthe residue was purified by column chromatography
- washeluting with a gradient from hexane to 80:20 hexane-EtOAc)
- dissolutionThe crude product was dissolved in EtOAc
- washthe solution was washed twice with 1 M aqueous sodium hydroxide and brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-61d4fe62efbe4134845799e7ecf48bcc
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362065B2
Reaction notes
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