3-Phenylprop-2-En-1-Ol → HCID 320666, compound

HRID 596986Notes

Reaction equation

HRID 596986 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10](O)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:10]([C:5]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[C:3]([OH:9])[CH:4]=1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 99584-MethylcatecholHCID 54670067L-Ascorbic Acid

Product 1

HCID 320666HCID 320666, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

A mixture of 1,2-dihydroxy-5-methylbenzene (124 g.) and cinnamyl alcohol (134 g.) in 2% aqueous citric acid (1.5 l.) containing ascorbic acid (10.0 g.) was boiled at reflux for 20 hours. After cooling, an oily layer separated and was collected and distilled to give 4-cinnamyl-5-methyl-1,2-dihydroxybenzene (119 g.) as a colorless oil, b.p. 205°-230° at 1.0 mm Hg. The oil was crystallized from a benzene/low-boiling petroleum ether (1/1) mixture to give colorless needles, m.p. 85°. Found: C, 79.9; H, 6.68. Calculated for C16H16O2 : C, 80.0; H, 6.71. The 100 MHz nuclear magnetic resonance (nmr) spectrum of this compound in deuterated chloroform exhibited a singlet (3 protons) at δ 2.07, a doublet (2 protons) at δ 3.37 (J = coupling constant = 5.0 Hz), a singlet (2 protons) at δ 5.02, a multiplet (2 protons) at δ 6.23-6.31, a singlet (1 proton) at δ 6.65, a singlet (1 proton) at δ 6.68, and a multiplet (5 protons) at δ 7.10-7.38.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureAfter cooling
  3. customan oily layer separated
  4. customwas collected
  5. distillationdistilled

Sources & evidence

ORD record
ord-98bddf9858534e1c8000b0cc54589da6
Source dataset
uspto-grants-1977_03
Patent number
US04012529

Reaction notes

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