Trimethyl orthoformate → 2-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile

HRID 64255Notes

Reaction equation

HRID 64255 reaction equation
[OH:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[C:3]([C:6]#[N:7])[C:4]#[N:5].[CH:21](OC)(OC)OC>>[CH3:21][O:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[C:3]([C:4]#[N:5])[C:6]#[N:7]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 223471552-(Hydroxy-(4-phenoxyphenyl)methylene)propanedinitrile

Product 1

HCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrileYield 47.5%

Procedure

A solution of 2-(hydroxy(4-phenoxyphenyl)methylene)malononitrile (50 g, 190.8 mmol) in CH(OMe)3 (500 mL) was heated to 75° C. for 16 hr. Then the mixture was concentrated to a residue and washed with MeOH (50 mL) to give 25 g (47.5%) of 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile as a yellow solid. 1H NMR (DMSO-d6) δ 7.70 (d, J=8.4 Hz, 2H), 7.52-7.45 (m, 2H), 7.28 (t, J=7.6 Hz, 1H), 7.22-7.06 (m, 4H), 3.93 (s, 3H). MS (ESI) m/e [M+1]+ 276.9.

Workup

  1. concentrationThen the mixture was concentrated to a residue
  2. washwashed with MeOH (50 mL)

Sources & evidence

ORD record
ord-c6d8525db9304a08845d99420f811913
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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