3-Hydroxybenzyl alcohol → HCID 22645476, compound

HRID 2414395Notes

Reaction equation

HRID 2414395 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:15]([O:14][C:12](=[O:13])[CH2:11][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22645476HCID 22645476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(hydroxymethyl)-phenol (50 g, 0.4 mol) and t-butyl bromoacetate (86 g, 0.44 mol) in DMF (500 ml, anhydrous) at room temperature is added K2CO3 (122 g, 0.88 mol). The reaction mixture is stirred vigorously for 2 hrs, and the mixture is poured into ice-water (2.5 L) and extracted with ether (3×500 ml). The combined ether extracts are washed with water, dried over MgSO4 and evaporated in vacuo to provide t-butyl-3-(hydroxymethyl)-phenoxyacetate as a low melting, light yellow solid; mp: 52-56° C.

Workup

  1. extractionextracted with ether (3×500 ml)
  2. washThe combined ether extracts are washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3295823a5684449cad72d580ca694b4c
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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