Ethanol → Ethyl [3-(hydroxymethyl)phenoxy]acetate

HRID 979543Notes

Reaction equation

HRID 979543 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9].C(Cl)(Cl)Cl.O.[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([O:10][CH2:19][CH3:20])=[O:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 6212ChloroformHCID 246028[3-(Hydroxymethyl)phenoxy]acetic acid

Product 1

HCID 18367402Ethyl [3-(hydroxymethyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 3-(hydroxymethyl)phenoxyacetic acid (3.18 g.) in ethanol (30 ml.) was treated with concentrated sulphuric acid (10 drops) and allowed to stand for 3 days. Chloroform (100 ml.) and water (50 ml.) were then added. The organic phase was separated, washed sequentially with saturated aqueous sodium hydrogen carbonate solution (2×50 ml.), water (50 ml.) and saturated brine (50 ml.) and then dried (MgSO4) The dried solution was evaporated and the residue purified by flash column chromatography, eluting with petrol (40°-60° )/ ethyl acetate (60:40 v/v) to give ethyl 3-(hydroxymethyl)phenoxyacetate (2.6 g.) as a colourless oil, NMR: 1.25 (3H,t), 2.8 (1H,br s), 4.25 (2H,q), 4.6 (4H,s) and 6.6-7.4 (4H,m)ppm.

Workup

  1. customThe organic phase was separated
  2. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution (2×50 ml.), water (50 ml.) and saturated brine (50 ml.)
  3. dry with materialdried (MgSO4) The dried solution
  4. customwas evaporated
  5. customthe residue purified by flash column chromatography
  6. washeluting with petrol (40°-60° )/ ethyl acetate (60:40 v/v)

Sources & evidence

ORD record
ord-596e1f7cd91f43478f86513da932557b
Source dataset
uspto-grants-1987_05
Patent number
US04668698

Reaction notes

Loading…