Sodium Hydroxide → HCID 14519922, compound

HRID 1198622Notes

Reaction equation

HRID 1198622 reaction equation
[CH2:1]([C:4]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:5]=1[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)[CH:2]=[CH2:3].[OH-].[Na+].C(C1C2C(=O)C3C(=CC=CC=3)OC=2C=CC=1C)C=C>C(Cl)(Cl)Cl>[CH2:1]([C:4]1[C:5]2[O:6][C:7]3[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:9](=[O:11])[C:16]=2[CH:17]=[C:18]([CH3:20])[CH:19]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14519921HCID 14519921, compoundHCID 53992191HCID 53992191, compound

Product 1

HCID 14519922HCID 14519922, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 13.6 g (70 mmol) potassium 2-chlorobenzoate, 14.3 g (84 mmol, 1.2 equiv.) sodium 2-allyl-4-methylphenoxide, 0.8 g (8 mmol) CuCl and 2.6 g (8 mmol) tris[2-(2-methoxyethoxy]amine (TDA-1) in 200 ml anisole was heated and stirred under reflux for 3 hours. The anisole was removed under vacuum and the residue was extracted with dilute aqueous ammonia. After filtration to remove insoluble inorganics the aqueous solution was washed twice with ethyl acetate to remove remaining traces of anisole and excess 2-allyl-4-methylphenol. Acidification with conc. hydrochloric acid then gave an oil which was extracted into ethyl acetate. The organic layer was dried (Na2SO4) and the ethyl acetate was removed to give 10.6 g (47% yield) of crude 2-(2-allyl-4-methylphenoxy)benzoic acid (XVIII; R1 =H; R3 =4'-CH3), as an oil. The oil was dissolved in 50 ml of a chloroform solution of polyphosphate ester (PPE) and heated on a waterbath with the solvent being allowed to boil off. After 30 min the residue was basified with dilute sodium hydroxide solution and the oil product was extracted into petroleum ether. After being dried (Na2SO4) the solvent was removed to give 6.5 g (66% yield) of 4-allyl-2-methylxanthenone (XIX: R1 =H; R3 =2-CH3 ; m.p. (methanol) 97°-98° C. Anal. (C17H14O2) C,H.

Workup

  1. extractionwas extracted into ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe ethyl acetate was removed
  4. temperatureheated on a waterbath with the solvent
  5. extractionthe oil product was extracted into petroleum ether
  6. dry with materialAfter being dried (Na2SO4) the solvent
  7. customwas removed

Sources & evidence

ORD record
ord-d34d18042fa84389a02ae403f8ddd04f
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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