4-Hydroxybenzyl Alcohol → HCID 59478957, compound

HRID 450776Notes

Reaction equation

HRID 450776 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].[N-:25]=[N+:26]=[N-:27].[Na+]>O.CN(C=O)C>[C:15]([O:14][C:12](=[O:13])[CH2:11][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:25]=[N+:26]=[N-:27])=[CH:4][CH:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 59478957HCID 59478957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.97 g of 4-(hydroxymethyl)phenol, 4.90 g of tert-butyl bromoacetate, and 25 ml of DMF was added 4.96 g of potassium carbonate at room temperature, followed by stirring for 12 hours. To the reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane) to obtain a pale yellow oily substance. This oily substance was subjected to methanesulfonylation in accordance with Production Example 15, and then reacted with sodium azide to obtain 4.03 g of tert-butyl[4-(azidomethyl)phenoxy]acetate as a pale yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane)
  6. customto obtain a pale yellow oily substance

Sources & evidence

ORD record
ord-2d3e493ec6c04292bbb67fc574b44c89
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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