3,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether → 2,6-Diphenyl-4-decyloxy-phenol

HRID 1743493

Reaction equation

HRID 1743493 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([O:24]COCCOC)=[C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(Cl)Cl.[Zn+2].[Br-].[Br-]>[C:31]1([C:14]2[CH:13]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:15]=2[OH:24])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 1

HCID 222374833,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether

Product 1

HCID 222375862,6-Diphenyl-4-decyloxy-phenolYield 79.1%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5-diphenyl-4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether (0.880 g, 1.793 mmol) and ZnBr2 (2.019 g, 8.967 mmol) in methylene chloride (10 ml) under nitrogen was stirred at room temperature. After ˜48 h, the reaction mixture was concentrated in vac and the residue was taken up in EtOAc (60 ml) and saturated NaHCO3 solution (20 ml). The layers were shaken and separated and the organic layer was washed with saturated NaHCO3 solution (2×10 ml), water (3×10 ml), brine (1×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 1% EtOAc/Hex) to give the product as a light brown oil (0.571 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 0.83–0.88 (m, 3H), 1.20–1.36 (m, 12H), 1.36–1.45 (m, 2H), 1.65–1.73 (m, 2H), 3.96 (t, J=6.6 Hz, 2H), 6.77 (s, 2H), 7.31–7.36 (m, 2H), 7.40–7.45 (m, 4H), 7.54–7.58 (m, 4H), 7.80 (s, 1H); IR (film) 3550, 2940, 1600, 1460, 1180 cm−1; mass spectrum [EI], m/z 402 M+.

Workup

  1. concentrationthe reaction mixture was concentrated in vac
  2. stirringThe layers were shaken
  3. customseparated
  4. washthe organic layer was washed with saturated NaHCO3 solution (2×10 ml), water (3×10 ml), brine (1×10 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vac
  8. customdried
  9. customThe residue was purified by flash chromatography (hexane and 1% EtOAc/Hex)

Sources & evidence

ORD record
ord-02f3d466c84e466982086440573fb9a1
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Linked notes

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