Toluene → HCID 57437182, compound

HRID 560281Notes

Reaction equation

HRID 560281 reaction equation
[CH2:1](Br)[C:2]#[CH:3].C1(C)C=CC=CC=1.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC.O>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:3][C:2]#[CH:1])[CH:16]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 57437182HCID 57437182, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of propargyl bromide in toluene (80%, 68.7 mmol, 7.40 mL) is added to a solution of 3-hydroxy-benzoic acid methyl ester (48.6 mmol) in DMF (45 mL). K2CO3 is added and the mixture is stirred at RT for 4 h. Water and ether are added, the layers are separated and the organic layer is washed with aq. NaOH solution (5%) and brine. The solvents are removed in vacuo to give the desired ester as a pale yellow solid. 1H-NMR (CDCl3): δ=2.56 (s, 1H); 3.94 (s, 3H); 4.76 (s, 2H); 7.20 (d, J=8.04 Hz, 1H); 7.39 (t, J=8.16 Hz, 1H); 7.66 (bs, 1H); 7.71 (d, J=7.78 Hz, 1H).

Workup

  1. customthe layers are separated
  2. washthe organic layer is washed with aq. NaOH solution (5%) and brine
  3. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-63de790407cb411a8a609f9b1b0178fd
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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