Methylparaben → HCID 14297705, compound

HRID 275243Notes

Reaction equation

HRID 275243 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[F:12][C@@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:12][C@@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11137325(S)-2-fluorooctane-1-ol

Product 1

HCID 14297705HCID 14297705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 mol of methyl 4-hydroxybenzoate, 0.1 mol of (S)-2-fluoro-1-octanol and 0.12 mol of triphenylphosphine are dissolved in 250 ml of tetrahydrofuran, and 0.12 mol of diethyl azodicarboxylate is added dropwise with stirring and ice cooling. The mixture is allowed to warm to room temperature, and is then stirred for a further 8 hours. The solvent is then distilled, and the methyl 4-(2-fluorooctyloxy)benzoate is purified by column chromatography. Saponification using aqueous/alcoholic potassium hydroxide solution gives (S)-4-(2-fluorooctyloxy)benzoic acid.

Workup

  1. stirringis then stirred for a further 8 hours
  2. distillationThe solvent is then distilled
  3. customthe methyl 4-(2-fluorooctyloxy)benzoate is purified by column chromatography

Sources & evidence

ORD record
ord-51a6dcce5cb84285a9623095259a50f0
Source dataset
uspto-grants-1995_02
Patent number
US05393459

Reaction notes

Loading…