Benzoic acid, 2-hydroxy-3-methyl-, methyl ester → HCID 14985947, compound

HRID 1669773Notes

Reaction equation

HRID 1669773 reaction equation
C([Li])CCC.[I-].[CH3:7][P+:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:27][C:28]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:29]=1[C:30](OC)=[O:31]>CCCCCC.C1COCC1>[OH:27][C:28]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:29]=1[C:30](=[O:31])[CH:7]=[P:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 638159Methyltriphenylphosphonium iodideHCID 178418339Butyllithium

Product 1

HCID 14985947HCID 14985947, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

206.8 ml (330.9 mmol) of a 1.6 molar n-butyllithium solution in n-hexane are slowly added to 97.3 g (240.7 mmol) of methyltriphenylphosphonium iodide in 800 ml of absolute THF under argon. The mixture is stirred at room temperature for 3 h. Then 20.0 g (120.3 mmol) of methyl 2-hydroxy-3-methylbenzoate in 200 ml of absolute THF are added dropwise to the reaction mixture. The mixture is stirred at 60° C. for 3 h. After cooling to room temperature, the precipitated lithium iodide is filtered off. The filtrate is concentrated in vacuo, and the residue is recrystallized from methanol. 27 g (56% of theory) of the title compound are obtained.

Workup

  1. stirringThe mixture is stirred at 60° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitated lithium iodide is filtered off
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-088457c3f90240a8959407b468b4f823
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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