Vanillin → HCID 965934, compound

HRID 1616785Notes

Reaction equation

HRID 1616785 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[O:13]=[CH:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:19][O:18][C:17]1[CH:16]=[C:15]([CH:23]=[CH:22][C:20]=1[O:21][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)[CH:14]=[O:13]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 703202-Bromomethylnaphthalene

Product 1

HCID 965934HCID 965934, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(Bromomethyl)naphthalene (1.3 g, 5.9 mmol) was added to a suspension of vanillin (0.60 g, 3.9 mmol) and potassium carbonate (1.6 g, 12 mmol) in acetone (10 mL) and treated according to Procedure 3. The crude product was recrystallised from EtOAc/petrol providing 3-methoxy-4-(naphth-2-ylmethoxy)benzaldehyde (0.87 g, 75%) as a colourless crystalline solid; mp 107-108° C.; δH (400 MHz, CDCl3) 3.97 (s, 3H, OCH3), 5.41 (s, 2H, OCH2), 7.38 (m, 1H, Naphth-H), 7.44 (d, J2,6=1.6 Hz, 1H, H2), 7.48-7.50 (m, 3H, H6, Naphth-H), 7.55 (m, 1H, Naphth-H), 7.83-7.89 (m, 4H, Naphth-H), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 56.3, 71.3 109.7, 112.8, 125.1 126.4, 126.5, 126.6, 126.8, 128.0, 128.2, 128.9, 130.6, 133.4, 133.5, 133.7, 150.4, 153.8, 191.1; vmax 991, 1131, 1263, 1505, 1580, 1672, 2884 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was recrystallised from EtOAc/petrol

Sources & evidence

ORD record
ord-f871a746e2f5428a9d678ea9f7c327a8
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

Loading…