Water → Ethyl [3-(3-hydroxypropyl)phenoxy]acetate

HRID 2389321Notes

Reaction equation

HRID 2389321 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CC#N>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 103518713-Hydroxybenzenepropanol

Product 1

HCID 86637895Ethyl [3-(3-hydroxypropyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(3-hydroxypropyl)phenol (100 g) in MeCN (750 mL) was added K2CO3 (109 g) at ambient temperature. Ethyl bromoacetate (87.4 mL) was added dropwise to the mixture at 0° C. over 30 minutes, and then the mixture was stirred at ambient temperature for 20 hours and at 60° C. for 7 hours. Water (800 mL) was added to the mixture at ambient temperature and the resulting mixture was extracted with EtOAc(1 L) two times. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to afford ethyl [3-(3-hydroxypropyl)phenoxy]acetate (121 g) as a colorless oil.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc(1 L) two times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-d40d2f86f2da46a5af754d1487b39401
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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