Veratryl alcohol → HCID 13117145, compound

HRID 978616Notes

Reaction equation

HRID 978616 reaction equation
[CH2:1]([CH:4]1[C:8](O)([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][OH:18].[H-].[Na+]>O1CCCC1>[CH2:1]([C:4]1[C:5](=[O:11])[CH2:6][CH:7]([O:18][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:8]=1[CH3:9])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7118Veratryl alcoholHCID 24758Sodium hydrideHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13117145HCID 13117145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Allyl-3-hydroxy-3-methyl-4-cyclopentenone (0.1 mol; 1 part) was dropwise added to a mixture of 3,4-dimethoxybenzyl alcohol (4 parts), tetrahydrofuran (4 parts) and sodium hydride (1/40 part) in the same flask as used in Example 1 at a temperature of 10° to 20° C. for 30 minutes. Then, the reaction mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the mixture was treated in the same manner as in Example 25 to obtain 2-allyl-3-methyl-4-(3,4-dimethoxybenzyloxy)-2-cyclopentenone. Yield, 96%. nD20 1.5514.

Workup

  1. customAfter completion of the reaction
  2. additionthe mixture was treated in the same manner as in Example 25

Sources & evidence

ORD record
ord-6a2d3a605c6d4f18be66e19ec35963ee
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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