Phenol → 8-Phenoxy-1,4-dioxaspiro[4.5]decane

HRID 1025730Notes

Reaction equation

HRID 1025730 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([O-])=O)=NC([O-])=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]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 51573101N-carboxylatoiminocarbamate

Product 1

HCID 189804238-Phenoxy-1,4-dioxaspiro[4.5]decaneYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (1.05 g, 6.63 mmol), phenol (0.75 g, 7.95 mmol), triphenylphosphine (1.91 g, 7.29 mmol) in CH2Cl2 (20 mL) was added disopropyl azodicarboxylate (1.57 mL, 7.95 mmol). After being stirred overnight at room temperature under N2, the reaction mixture was concentrated. The residue was flash chromatographed using 10:90 hexane-EtOAc to give 1.09 g of 8-phenoxy-1,4-dioxaspiro[4.5]decane. MS (EI) calcd: (M+H)+=235.1; found: 235.0.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-a0166c0a06ad489780e584a7732923f2
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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