Naphthalen-1-ethanol → 2-(1-Naphthyl)ethyl 3,4-dihydroxycinnamate

HRID 976035Notes

Reaction equation

HRID 976035 reaction equation
[C:1]([OH:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[C:14]1([CH2:24][CH2:25]O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>>[C:14]1([CH2:24][CH2:25][O:12][C:1](=[O:13])/[CH:2]=[CH:3]/[C:4]2[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 13047Naphthalen-1-ethanolHCID 689043Caffeic Acid

Product 1

HCID 54685192-(1-Naphthyl)ethyl 3,4-dihydroxycinnamate

Procedure

Reaction of caffeic acid and 2-(1-naphthyl)ethanol as outlined in method A except that the reaction time was increased to 6 days, provided product 67H-148-A as a snow-white solid in 21% overall yield: mp 165°-168° C.; 1H NMR (DMSO-d6) δ:8.21 (d, 1H, J=8.1 Hz), 7.97-7.94 (m, 1H), 7.84 (t, 1H, J=5 Hz), 7.64-7.39 (m, 5H), 7.03 (d, 1H, J=1.8 Hz), 6.99 (dd, 1H, J=1.8 Hz & 8.1 Hz), 6.23 (d, 1H, J=15.9 Hz), 4.44 (t, 2H, J=7.0 Hz), 3.45 (t, 2H, J=7.0 Hz); FABMS (NBA, -VE) m/z 333 (M--H). Anal. (C21H18O4.1/4H2O) C, H.

Workup

  1. temperaturewas increased to 6 days
  2. customprovided product 67H-148-A as a snow-white solid in 21% overall yield

Sources & evidence

ORD record
ord-1c57c57ae0a14645900ae812522d50b3
Source dataset
uspto-grants-1997_03
Patent number
US05610185

Reaction notes

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