Benzyltrimethylammonium hydroxide → 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid

HRID 435850Notes

Reaction equation

HRID 435850 reaction equation
[OH:1][C:2]1[C:11]2[O:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8][C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:18]([C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[O:24][CH2:25][CH:26]1[O:28][CH2:27]1)([CH3:21])([CH3:20])[CH3:19].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN(C)C=O>[C:18]([C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[O:24][CH2:25][CH:26]([OH:28])[CH2:27][O:1][C:2]1[C:11]2[O:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1)([CH3:19])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 66854Benzyltrimethylammonium hydroxideHCID 516892Sodium BicarbonateHCID 30162201-tert-Butyl-2-(2,3-epoxypropoxy)benzeneHCID 12355847ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate

Product 1

HCID 130909888-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 16.7 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 14.7 parts of 3-(2-t-butylphenoxy)-1,2 -epoxypropane, 50 parts of dimethyl formamide, and 0.1 parts of benzyltrimethyl ammonium hydroxide was boiled under reflux for 3 hours, evaporated to leave a dark brown oil, and treated with ethyl acetate, which was then washed with 2% sodium hydroxide solution, and water, dried, and evaporated to an oil. The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which was boiled with an aqueous ethanolic solution of sodium bicarbonate. The mixture was acidified to give a solid, which was recrystallised from ethanol after treatment with charcoal to give 4.6 parts of 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid as a cream solid, mp. 227°-228° (decomp.).

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated
  3. customto leave a dark brown oil
  4. washwas then washed with 2% sodium hydroxide solution, and water
  5. customdried
  6. customevaporated to an oil
  7. customThe oil was chromatographed on a silica column with chloroform as eluent
  8. customto give a gummy solid, which
  9. customto give a solid, which
  10. customwas recrystallised from ethanol after treatment with charcoal

Sources & evidence

ORD record
ord-c0ffb82b83ad4fa39aa0aac15c5b13ef
Source dataset
uspto-grants-1977_02
Patent number
US04006245

Reaction notes

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