Thionyl Chloride → HCID 86700498, compound

HRID 589534Notes

Reaction equation

HRID 589534 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH:28]([CH3:30])[CH3:29])[CH:22]=1)([CH3:20])([CH3:19])[CH3:18].S(Cl)(Cl)=O>CO>[CH:10]([C:9]1[C:8]([OH:13])=[C:7]([CH:14]([CH3:15])[CH3:16])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:12]=1)([C:9]1[C:8]([OH:13])=[C:7]([CH:14]([CH3:16])[CH3:15])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[CH:12]=1)[C:25]1[C:24]([OH:27])=[C:23]([CH:28]([CH3:30])[CH3:29])[CH:22]=[C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:26]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 12857377HCID 12857377, compoundHCID 20206379HCID 20206379, compound

Product 1

HCID 86700498HCID 86700498, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound 3 was synthesized as described elsewhere with minor modifications.6 Briefly, a sample of 5-(tert-butyl)-2-hydroxy-3-isopropylbenzaldehyde (2) (5.08 g, 24.3 mmol) was combined with 2 equivalents of 4-(tert-butyl)-2-isopropylphenol (1) (9.17 g, 47.7 mmol) and 14 mL of methanol in a 100 mL schlenk flask. With a sodium carbonate trap connected to the reaction flask, the reaction mixture was cooled to 0° C. and thionyl chloride (11.4 mL, 157.7 mmol) was added dropwise causing an immediate change from orange/yellow to dark purple for the reaction mixture. The reaction was stirred overnight. The precipitate that was formed was collected by filtration. The residue was recrystallized from hexanes to afford 3 as a pale purple solid (6.88 g) in 48% yield with respect to the starting salicylaldehyde. 1H NMR (CDCl3-d) δ ppm 1.20 (27 H, s), 1.26 (18 H, d, J=6.9 Hz), 3.22 (3 H, spt, J=6.9 Hz), 4.91 (3 H, s), 5.83 (1 H, s), 6.81 (3 H, d, J=2.3 Hz), 7.18 (3 H, d, J=2.3 Hz). 13C-{1H} NMR, δ 22.7, 27.5, 31.4, 34.3, 41.8, 122.2, 123.7, 125.7, 135.0, 143.5, 148.9. Anal. calcd. for C40H58O3: C, 81.86; H, 9.96; N, 0.00. Found: C, 81.79; H, 10.32; N, 0.00.

Workup

  1. customCompound 3 was synthesized
  2. customWith a sodium carbonate trap connected to the reaction flask
  3. customThe precipitate that was formed
  4. filtrationwas collected by filtration
  5. customThe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-0a8d9e1bbcc24ee6baa34cb6e217193a
Source dataset
uspto-grants-2016_01
Patent number
US09233364B2

Reaction notes

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