2,4-Dihydroxybenzoic Acid → Phenylmethyl 2,4-bis(phenylmethoxy)benzoate

HRID 1354813Notes

Reaction equation

HRID 1354813 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:18]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][C:2]=1[O:1][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14912,4-Dihydroxybenzoic AcidHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 15087000Phenylmethyl 2,4-bis(phenylmethoxy)benzoateYield 155.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-dihydroxy-benzoic acid (35) (2 g, 13 mmol) in THF (250 mL) was mixed with cesium carbonate (16.9 g, 52 mmol) and benzyl bromide (6.2 mL, 52 mmol). The reaction mixture was refluxed overnight and then cooled down to room temperature. Cesium carbonate was filtered off through filter paper. The solvent was removed under reduced pressure. Liquid-liquid extraction was performed using 200 mL of CHCl3 and H2O (100 mL×3). The organic layer was dried over MgSO4. After filtering off the MgSO4, the organic layer was concentrated to give compound 36 (4.3 g) as a solid. LC-MS (ESI): m/e=425.2 [M+1]+

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationCesium carbonate was filtered off
  3. filtrationthrough filter paper
  4. customThe solvent was removed under reduced pressure
  5. extractionLiquid-liquid extraction
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationAfter filtering off the MgSO4
  8. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-8dcdbb90bc0f46eba7def5eee8ab4c36
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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