Phenol → HCID 89581351, compound

HRID 1501240Notes

Reaction equation

HRID 1501240 reaction equation
[OH:1][CH2:2][CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O-:11])=[O:10])=[CH:7][CH:6]=1)[CH3:4].[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[O:1]([CH2:2][CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:21])=[O:10])=[CH:7][CH:6]=1)[CH3:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 131734280HCID 131734280, compound

Product 1

HCID 89581351HCID 89581351, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-hydroxypropan-2-yl)benzoate (100 mg, 0.52 mmol), phenol (78 mg, 0.8 mmol), triphenylphosphine (216 mg, 0.8 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (166 mg, 0.8 mmol) at room temperature. The mixture solution was stirred for 18 hours. Then tetrahydrofuran was removed in vacuo. The residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=6:1) to give methyl 4-(1-phenoxypropan-2-yl)benzoate as a colorless oil (100 mg, 71%). 1H NMR (300 MHz, CDCl3): δ 7.98 (d, J=9 Hz, 2H), 7.37 (d, J=9 Hz, 2H), 7.23-7.29 (m, 2H), 6.85-6.95 (m, 3H), 3.98-4.11 (m, 2H), 3.91 (s, 3H), 3.27-3.34 (m, 1H), 1.43 (d, J=6 Hz, 2H).

Workup

  1. customThen tetrahydrofuran was removed in vacuo
  2. customThe residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-aae82fd5539342ab93d44f1c0bd53b10
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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