Water → HCID 24825726, compound

HRID 1925085Notes

Reaction equation

HRID 1925085 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[CH2:21]O)=[C:5]([CH2:23][OH:24])[CH:4]=1.O.C(OCC)(=O)C>C1COCC1.Cl>[CH3:12][O:11][C:7]1[C:6]2[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[CH2:21][O:24][CH2:23][C:5]=2[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 281677HCID 281677, compound

Product 1

HCID 24825726HCID 24825726, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4,4′,5,6-tetramethoxybiphenyl-2,2′-diyl)dimethanol (170 mg, 0.51 mmol) in THF (2 mL), 2M HCl (2 mL) and concentrated hydrochloric acid (1 mL) was stirred under reflux for 3 hours. Water (15 mL) and ethyl acetate (15 mL) were added to the reaction mixture, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The extracts were combined, dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography of the residue over silica gel (20 g), eluting with hexane-ethyl acetate (4:1), yielded the title compound as a white solid (150 mg, 93%); m.p. 151-153° C.; Elemental Analysis Found: C, 68.5; H, 6.5 (C18H20O5 requires C, 68.34; H, 6.37%); NMR Spectrum δH (300 MHz, CDCl3) 7.63 (1H, d, J 8.4 Hz, 11-H), 6.98 (1H, dd, J 2.6, 8.4 Hz, 10-H), 6.96 (1H, d, J 2.6 Hz, 8-H), 6.75 (1H, s, 4-H), 4.42 (2H, m), 4.08 (2H, m), 3.94 (3H, s, OCH3), 3.91 (3H, s, OCH3), 3.86 (3H, s, OCH3), 3.65 (3H, s, OCH3); NMR Spectrum δC (75 MHz, CDCl3) 55.7, 56.4, 61.2, 61.5, 68.1, 109.1, 114.2, 114.8, 126.7, 129.7, 131.1, 131.4, 136.8, 143.1, 150.9, 153.1, 159.4; νmax/cm−1 (thin film) 2963, 2936, 2858, 2839, 1612, 1491, 1456, 1332, 1243, 1150, 1104, 1052, 1006; m/z (ES) 380 (MNa2H2O+, 100%), 287 (MH+—CH2O, 100); Rf (hexane-ethyl acetate 3:1) 0.39.

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash chromatography of the residue over silica gel (20 g), eluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-0459ba3f8cc54162b6fe2add13a87922
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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