Neopentyl glycol → HCID 14403835, compound

HRID 1194136Notes

Reaction equation

HRID 1194136 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[CH:12]=[O:13].[CH3:14][C:15]([CH3:20])([CH2:18]O)[CH2:16][OH:17]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[CH:12]1[O:17][CH2:16][C:15]([CH3:20])([CH3:18])[CH2:14][O:13]1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 14403834HCID 14403834, compound

Product 1

HCID 14403835HCID 14403835, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1.00 g (4.19 mmol) of (E)-3-(2-bromo-4,6-dimethylphenyl)-2-propenal, 1.32 g (12.6 mmol) of 2,2-dimethyl-1,3-propanediol and a catalytic amount (65 mg) of p-toluenesulfonic acid monohydrate in 100 mL of dry benzene was heated at reflux in a Dean-Stark apparatus for 2 hours. The solution was washed with 1N sodium hydroxide, water (3 times), and the solvent removed under reduced pressure to give 1.32 g (97%) of (E)-2-[2-(2-bromo-4,6-dimethylphenyl)ethenyl]-5,5-dimethyl-1,3-dioxane as a white crystalline material. Purification by HPLC (70% CH2Cl2 -Hexane) gave an analytically pure sample: mp 54°-56° C.; IR (KBr) 2960, 2860, 1670 and 1610 cm-1 ; NMR (CDCl3) δ 0.77 (3H, s), 1.25 (3H, s), 2.28 (3H, s), 2.37 (3H, s), 3.58 (2 H, d, J=12 Hz), 3.74 (2H, d, J=12 Hz), 5.09 (1H, d, J=6 Hz), 5.90 (1H, dd, J=6, 15 Hz), 6.78 (1H, d, J=15 Hz), 6.96 (1H, s), 7.30 (1H, s).

Workup

  1. temperatureat reflux in a Dean-Stark apparatus for 2 hours
  2. washThe solution was washed with 1N sodium hydroxide, water (3 times)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8e1bebe5b3d5424da48d2852b0e18b44
Source dataset
uspto-grants-1989_03
Patent number
US04812583

Reaction notes

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