Thiodiglycol → HCID 22949955, compound

HRID 1700936Notes

Reaction equation

HRID 1700936 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[S:14]([CH2:18][CH2:19]O)[CH2:15][CH2:16][OH:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1.CCOCC>[OH:17][CH2:16][CH2:15][S:14][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5447ThiodiglycolHCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22949955HCID 22949955, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
22 °C

Procedure

A solution of methyl 3-[4-hydroxyphenyl)propionate (30.0 g, 0.166 mol), 2,2′-thiodiethanol (61.0 g, 0.50 mol) and triphenylphosphine (48.0 g, 0.183 mol) in dry benzene (450 ml) was treated at 22° C. with diethyl azodicarboxylate (33.2 g, 0.19 mol) added dropwise over 10 min and the resulting mixutre was stirred at 22° C. for 5 h. The reaction mixture was then diluted with ether (300 ml) washed with water, saturated sodium bicarbonate and brine. After drying (magnesium sulfate) the solvent was evaporated in vacuo and the residue was chromatographed on silica gel (elution toluene-ethyl acetate 85:15) to give 37.64 g (79%) of the starting material as a white solid: mp 47-48° C.

Workup

  1. additionadded dropwise over 10 min
  2. washwashed with water, saturated sodium bicarbonate and brine
  3. dry with materialAfter drying (magnesium sulfate) the solvent
  4. customwas evaporated in vacuo
  5. customthe residue was chromatographed on silica gel (elution toluene-ethyl acetate 85:15)

Sources & evidence

ORD record
ord-adf3de62546f4bf2bf8e2b406c579db5
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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