Hydrochloric Acid → HCID 90408745, compound

HRID 2275413Notes

Reaction equation

HRID 2275413 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:14])[C:5]=1[OH:15])[CH:2]=[CH2:3].CC([O-])(C)C.[K+].C1COCC1.Cl>CS(C)=O>[OH:15][C:5]1[C:6]([CH3:14])=[C:7]([CH:12]=[CH:13][C:4]=1[CH:1]=[CH:2][CH3:3])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 67404181HCID 67404181, compound

Product 1

HCID 90408745HCID 90408745, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

In a round bottom flask fitted with a dropping funnel was added methyl 4-allyl-3-hydroxy-2-methylbenzoate (4.12 g, 20 mmol) in anhydrous DMSO (20 ml) at room temperature under argon. t-BuOK in 1.0 M THF (5.61 g, 50 mmol) was added drop wise to the stirred solution. After the addition, the reaction mixture was heated at 55° C. overnight. The reaction was monitored using LCMS. After the reaction was complete, it is cooled, acidified with 1N HCl and stirred for 30 min. Aqueous work up and extraction with ethyl acetate gave the crude mixture which was purified using an ISCO system (40 g silica gel column, hexane/EtOAc solvent gradient) to give 4.12 g (77%) of the product. 1H NMR (400 MHz, CDCl3) δ 7.42 (d, J=8.2 Hz, 1H), 7.18 (d, J=8.2 Hz, 1H), 6.61 (dd, J=15.9, 1.7 Hz, 1H), 6.37-6.13 (m, 1H), 3.90 (s, 3H), 2.50 (s, 3H), 1.96 (dd, J=6.6, 1.7 Hz, 3H).

Workup

  1. customIn a round bottom flask fitted with a dropping funnel
  2. additionAfter the addition
  3. temperatureit is cooled
  4. extractionAqueous work up and extraction with ethyl acetate
  5. customgave the crude mixture which
  6. customwas purified

Sources & evidence

ORD record
ord-c07f1e9681104e9fa4647e352d902277
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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