4-Chloro-1-naphthol → 2-Chloro-1-(4-((4-chloronaphthyloxy)methyl)phenoxy)ethane

HRID 1296848Notes

Reaction equation

HRID 1296848 reaction equation
BrCCOC1C=CC(CO)=CC=1.[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=1.[Cl:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](O)=[CH:28][CH:27]=1.C(P(CCCC)CCCC)CCC>C1COCC1>[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:26]([Cl:25])=[CH:27][CH:28]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 117874-Chloro-1-naphtholHCID 13831TributylphosphineHCID 21882321[4-(2-Chloroethoxy)phenyl]methanolHCID 22482237(4-(2-Bromoethoxy)phenyl)methanol

Product 1

HCID 235143952-Chloro-1-(4-((4-chloronaphthyloxy)methyl)phenoxy)ethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 8.4 grams (0.045 mole) of the mixture of (4-(2-bromoethoxy)phenyl)methan-1-ol and (4-(2-chloroethoxy)phenyl)methan-1-ol, 8.1 grams (0.045 mole) of 4-chloronaphthol, and 13.7 mL (0.054 mole) of tributylphosphine in 500 mL of THF was cooled in an ice bath and 12.6 grams (0.049 mole) of 1-1′-(azodicarbomyl)dipiperidine was added. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for 24 hours. After this time, the solvent was reduced under reduce pressure, yielding a solid. The solid was purified by column chromatography on silica gel, yielding 15 grams of crude product. The crude product was further purified by column chromatography on silca gel, yielding 6.7 grams of title compound.

Workup

  1. additionUpon completion of addition
  2. customyielding a solid
  3. customThe solid was purified by column chromatography on silica gel
  4. customyielding 15 grams of crude product
  5. customThe crude product was further purified by column chromatography on silca gel

Sources & evidence

ORD record
ord-82d21bd388de45c68246bab1be70f9be
Source dataset
uspto-grants-2007_07
Patent number
US07247756B2

Reaction notes

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