Veratraldehyde → HCID 23089836, compound

HRID 2222365Notes

Reaction equation

HRID 2222365 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH:23]=O>>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[CH:23]=[C:6](/[C:5]2[CH:9]=[CH:10][C:2]([O:1][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:3][CH:4]=2)\[C:7]#[N:8])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

4

Reactant 3

HCID 8419VeratraldehydeHCID 265484-Hydroxybenzyl cyanideHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 23089836HCID 23089836, compoundYield 81%

Procedure

The hydroxyl group of 4-hydroxybenzyl cyanide (26.63 g) was protected by use of 2-methoxyethoxymethyl chloride (24.42 g) in accordance with (production process 1), to thereby produce an MEM form (24.39 g, yield: 55%). The resultant MEM form (22.13 g) and 3,4-dimethoxybenzaldehyde (16.62 g) were subjected to condensation in accordance with process A of (production process 2), to thereby produce the target product (29.79 g, yield: 81%).

Workup

  1. customto thereby produce an MEM form (24.39 g, yield: 55%)

Sources & evidence

ORD record
ord-38f88c24de7143018167f7bf3b946bb9
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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