3,4-Dimethoxy-β-methyl-2-propylbenzenebutanoic acid → HCID 10825371, compound

HRID 1955368Notes

Reaction equation

HRID 1955368 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:18][CH2:19][CH3:20])=[C:5]([CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:18][CH2:19][CH3:20])=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:14](=[O:16])[CH2:13][CH:12]([CH3:17])[CH2:11]2

Participants

3

Reactant 1

HCID 105168773,4-Dimethoxy-β-methyl-2-propylbenzenebutanoic acid

Product 1

HCID 10825371HCID 10825371, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 15b (7.0 g, 25 mmol) was added to 35 g of polyphosphoric ester in 100 mL of methylene chloride and refluxed for 1 h. The reaction mixture was poured onto ice, stirred, and extracted with ether. The ether was evaporated, and the residual oil was chromatographed on silica gel using ethyl acetate/hexane to give 5.63 g (21.5 mmol, 86% yield) of 16b as white crystals: 1H NMR:(ppm) 7.49 (s, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.00-2.23 (mult, 7H), 1.50 (mult, 2H), 1.15 (d, 3H), 1.01 (t, 3H). Anal. (C16H22O3) C,H.

Workup

  1. temperaturerefluxed for 1 h
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted with ether
  4. customThe ether was evaporated
  5. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-7ab7e3fea90d4321893a98cbf4b489ca
Source dataset
uspto-grants-2000_09
Patent number
US06124498

Reaction notes

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