Water → HCID 57742154, compound

HRID 1626866Notes

Reaction equation

HRID 1626866 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:17][O:18][CH3:19].O>C1COCC1>[CH3:17][O:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 572437Ethyl (3-Hydroxyphenyl)acetate

Product 1

HCID 57742154HCID 57742154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(3-hydroxyphenyl)acetate (24 g, 80.51 mmol) in THF (100 mL) was slowly added sodium hydride (2.93 g, 73.3 mmol) and chloromethylmethylether (5.94 g, 73.7 mmol) at 0° C. The reaction mixture was stirred for 16 hours at room temperature. The mixture was added water (200 mL) and extracted with EtOAc. The organic layer was dried with MgSO4. The organic layer was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=10/1.

Workup

  1. customat 0° C
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationThe organic layer was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=10/1

Sources & evidence

ORD record
ord-f02dd8ad926249ff9d24eddd3742efa7
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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