M-Cresol → HCID 89580756, compound

HRID 1501040Notes

Reaction equation

HRID 1501040 reaction equation
[OH:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:32]1[C:37](O)=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:39].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:33]1([CH3:39])[CH:34]=[CH:35][CH:36]=[C:37]([O:1][CH:2]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=2)[CH3:3])[CH:32]=1

Participants

6

Reactant 4

HCID 342M-CresolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 22731454HCID 22731454, compound

Product 1

HCID 89580756HCID 89580756, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-(1-hydroxyethyl)benzoate (300 mg, 1.67 mmol) in tetrahydrofuran (50 mL) was added triphenylphosphine (569 mg, 2.17 mmol) and m-cresol (180 mg, 1.67 mmol), the solution was stirred for 30 minutes at room temperature, then diisopropylazodicarboxylate (438 mg, 2.17 mmol) was added dropwise to the solution at 0° C., the mixture was stirred at room temperature for 12 hours. Then the mixture was concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give methyl 4-(1-(m-tolyloxy)ethyl)benzoate (148 mg 33%) as oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. concentrationThen the mixture was concentrated
  3. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-8006a56747094008824d4c400475a9c0
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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