Ethanolamine → HCID 19108703, compound

HRID 1613816Notes

Reaction equation

HRID 1613816 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([CH2:18][NH2:19])[OH:17].[SH:20][CH2:21][C:22](O)=[O:23]>C1C=CC=CC=1>[OH:17][CH2:16][CH2:18][N:19]1[C:22](=[O:23])[CH2:21][S:20][CH:11]1[C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 1133Thioglycolic AcidHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 19108703HCID 19108703, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 15.3 g (0.077 mole) of 3-phenoxybenzaldehyde (Fluka), 4.8 g (0.078 mole) of ethanolamine (99%, Aldrich) and 7.5 g (0.077 mole) of mercaptoacetic acid (95%, Aldrich) in 150 ml of benzene was stirred and heated at reflux temperature overnight utilizing a Dean-Stark trap to remove water. The reaction mixture was poured into a solution of 300 ml of water and 20 ml of concentrated ammonium hydroxide solution. The layers were separated and the organic layer was washed twice with 100 ml portions of 2N hydrochloric acid, twice with 100 ml portions of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to give 23.6 g (97%) of the alcohol which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature overnight
  3. customto remove water
  4. additionThe reaction mixture was poured into a solution of 300 ml of water and 20 ml of concentrated ammonium hydroxide solution
  5. customThe layers were separated
  6. washthe organic layer was washed twice with 100 ml portions of 2N hydrochloric acid, twice with 100 ml portions of water
  7. dry with materialdried (magnesium sulfate)
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b44459dfca542babc822c0f259ec132
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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