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

HRID 1016018Notes

Reaction equation

HRID 1016018 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-9c2d8a2569b74a79aa4493950e31dd58
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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