3-Methyl-2-buten-1-OL → 2-[(3-Methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione

HRID 356137Notes

Reaction equation

HRID 356137 reaction equation
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:45][C:46]([CH3:50])=[CH:47][CH2:48]O>O1CCCC1>[CH3:45][C:46]([CH3:50])=[CH:47][CH2:48][O:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 111733-Methyl-2-buten-1-OLHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516607HCID 178516607, compound

Product 1

HCID 2616032-[(3-Methylbut-2-en-1-yl)oxy]naphthalene-1,4-dioneYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-hydroxynaphthalene-1,4-dione (10.0 g, 57.4 mmol) and triphenylphosphine (15.1 g, 57.4 mmol) in dry tetrahydrofuran (150 ml) at 0° C. under an atmosphere of nitrogen was added diethyl azodicarboxylate (10.0 g, 57.4 mmol). After stirring for a further 5 minutes, a solution of 3-methylbut-2-enol (7.42 g, 86.1 mmol) in dry tetrahydrofuran (10 ml) was added dropwise and stirring was continued for 2 hours. The precipitate was collected, air-dried and recrystallised from aqueous methanol to yield the title compound (8.3 g) as a yellow crystalline solid with a melting point of 138° C.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. customThe precipitate was collected
  4. customair-dried
  5. customrecrystallised from aqueous methanol

Sources & evidence

ORD record
ord-292ed9544c194591a2b400386badda62
Source dataset
uspto-grants-1998_11
Patent number
US05834515

Reaction notes

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