Water → HCID 24959799, compound

HRID 1925088Notes

Reaction equation

HRID 1925088 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([C:9]2[C:10]([CH2:18]O)=[CH:11][C:12]3[O:16][CH2:15][O:14][C:13]=3[CH:17]=2)=[C:7]([O:20][CH3:21])[C:6]([O:22][CH3:23])=[C:5]([O:24][CH3:25])[CH:4]=1.O.C(OCC)(=O)C>C1COCC1.Cl>[CH3:21][O:20][C:7]1[C:8]2[C:9]3[CH:17]=[C:13]4[O:14][CH2:15][O:16][C:12]4=[CH:11][C:10]=3[CH2:18][O:1][CH2:2][C:3]=2[CH:4]=[C:5]([O:24][CH3:25])[C:6]=1[O:22][CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 44579076HCID 44579076, compound

Product 1

HCID 24959799HCID 24959799, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-(6-(hydroxymethyl)-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxol-5-yl)methanol (170 mg, 0.48 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, 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), followed by crystallisation (ethyl acetate) yielded the title compound as large clear crystals (103 mg, 64%); m.p. 154-156° C.; Elemental Analysis Found: C, 65.3; H, 5.5 (C18H18O6 requires C, 65.45; H, 5.49%); NMR Spectrum δH (300 MHz, CDCl3) 7.21 (1H, s, 12-H), 6.98 (1H, s, 8-H), 6.96 (1H, s, 4-H), 6.75 (1H, s, 4-H), 6.04 (2H, d, J 4.8 Hz, 10-H2), 4.40 (2H, d, J 11.2 Hz, 5-H2), 4.04 (1H, d, J 10.8 Hz, 7-HA), 4.01 (1H, d, J 10.8 Hz, 7-HB), 3.96 (3H, s, OCH3), 3.91 (3H, s, OCH3), 3.71 (3H, s, OCH3); NMR Spectrum δC (75 MHz, CDCl3) 56.3, 61.2, 61.5, 67.6, 67.8, 101.6, 109.0, 109.9, 110.2, 126.8, 129.5, 131.3, 131.7, 143.0, 147.3, 147.7, 150.8, 153.3; νmax/cm−1 (thin film) 2967, 2932, 2866, 1600, 1484, 1460, 1414, 1324, 1239, 1146, 1107, 1045; m/z (ES) 301 (MH+—CH2O, 100%); Rf (hexane-ethyl acetate 4:1) 0.28.

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)
  8. customfollowed by crystallisation (ethyl acetate)

Sources & evidence

ORD record
ord-af42c65c8a3e49cf8a573c8422857cc6
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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