Triphenylphosphine → HCID 20745894, compound

HRID 2308122Notes

Reaction equation

HRID 2308122 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:9][O:10][C:11](=[O:23])[C:12]1[CH:21]=[C:20](O)[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[C:20]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:21]=[C:12]([C:11]([O:10][CH3:9])=[O:23])[CH:13]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 748286-Chloro-1-hexanolHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 20745894HCID 20745894, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

13.02 g (95.3 mmol) of 6-chlorohexanol were added to a solution of 20.04 g (95.3 mmol) of 5-hydroxyisophthalic acid dimethyl ester and 47.4 g (180.5 mmol) of triphenylphosphine in 300 ml of tetrahydrofuran. The colourless solution was cooled to 0° C. and then 79 ml (180.5 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise over a period of 2 hours and 45 minutes. The mixture was allowed to react for another 30 minutes at 0° C. and then for 22 hours at room temperature. The reaction mixture was concentrated by evaporation under vacuum. The residue was filtered through silica gel using dichloromethane:diethylether (85:15) as eluent. The filtrate was concentrated in vacuum and further purified by column chromatography on silica gel with hexane:ethyl acetate (9:1) to give 17.12 g (55%) of 5-[(6-chlorohexyl)oxy]isophthalic acid dimethyl ester as a white solid.

Workup

  1. customto react for another 30 minutes at 0° C.
  2. concentrationThe reaction mixture was concentrated by evaporation under vacuum
  3. filtrationThe residue was filtered through silica gel
  4. concentrationThe filtrate was concentrated in vacuum
  5. customfurther purified by column chromatography on silica gel with hexane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-42cb82dd8dac4a64ad9fb6c5795cefef
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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