(4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone → 4-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methanol

HRID 1647311Notes

Reaction equation

HRID 1647311 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9]>C(O)C>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH:8]([C:7]2[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:5]([O:4][CH3:3])[CH:6]=2)[OH:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 368149(4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)methanoneHCID 4311764Sodium borohydride

Product 1

HCID 3681404-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methanolYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (76 mg, 2 mmol) was added in small portions to a well-stirred solution of 3,4,4',5-tetramethoxybenzophenone (27) (302 mg, 1 mmol) in ethanol (15 mL) at 0° C. in 15 min and the resultant mixture was stirred for 3 h at room temperature. The reaction was quenched by careful addition of glacial acetic acid (1 mL), and the solvents were removed at reduced pressure. The residue was poured into water, and the product was extracted with ether (2×50 mL). The combined ether extracts were washed with saturated NaHCO3 solution, followed by water, and dried (Na2SO4). Evaporation of solvents and crystallization of the residue from EtOAc-hexane gave product 28 as a white crystalline solid (287 mg, 94%); mp 104°-105° C.; 1H NMR (CDCl3, 200 MHz) δ7.29 (d, J=8.7 Hz, 2H), 6.88 (d, J=8.7 Hz, 2H), 6.60 (s, 2H), 5.73 (d, J=3.2 Hz, 1H), 3.82 (s, 9H), 3.80 (s, 3H), 2.32 (d, J=3.2 Hz, 1H); CIMS (isobutane) m/e 305 (MH+, 100). Anal. (C17H20O5) C, H.

Workup

  1. customThe reaction was quenched by careful addition of glacial acetic acid (1 mL)
  2. customthe solvents were removed at reduced pressure
  3. additionThe residue was poured into water
  4. extractionthe product was extracted with ether (2×50 mL)
  5. washThe combined ether extracts were washed with saturated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvents and crystallization of the residue from EtOAc-hexane

Sources & evidence

ORD record
ord-59041b614c154889bac8fe0b92989de0
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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