Water → HCID 70154017, compound

HRID 1250100Notes

Reaction equation

HRID 1250100 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=1.[C:15]1([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:22](=[O:23])[N:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 65741N,N-Diphenylcarbamic chlorideHCID 21554300Acetic acid, 2-[3-(hydroxymethyl)phenoxy]-, methyl ester

Product 1

HCID 70154017HCID 70154017, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3-Hydroxymethylphenoxy)acetic acid methyl ester (400 mg, 2 mmol) and diphenylcarbamyl chloride (580 mg, 2.5 mmol) were combined in pyridine (2 ml). The resultant yellow solution was allowed to stand for ten days under nitrogen. The mixture was then poured into water, extracted with dichloromethane, and evaporated. Purification of the residue by silica gel chromatography, eluting with 5% acetone/dichloromethane, gave {3-[(diphenyl-carbamoyloxy)methyl]phenoxy}acetic acid methyl ester as a colorless solid (575 mg, 73%).

Workup

  1. waitto stand for ten days under nitrogen
  2. extractionextracted with dichloromethane
  3. customevaporated
  4. customPurification of the residue by silica gel chromatography
  5. washeluting with 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-a032ae42ede2422c87a0821e26570e01
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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