Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 425233, compound

HRID 2051918Notes

Reaction equation

HRID 2051918 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.C[O-:33].[Na+].Br[C:36]([CH3:43])([CH3:42])[C:37]([O:39]CC)=[O:38]>CN(C)P(N(C)C)(N(C)C)=O.[OH-].[Na+]>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:33][C:36]([CH3:43])([CH3:42])[C:37]([OH:39])=[O:38])=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 10942334Sodium MethoxideHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 425233HCID 425233, compound

Reagents, catalysts & solvents 2

HCID 12679HexamethylphosphoramideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 10.0 g of hydroquinone monobenzyl ether in 40 ml of hexamethylphosphoramide is added 2.7 g of sodium methoxide. The mixture is stirred 10 minutes and 10.3 g of ethyl 2-bromoisobutyrate is added. The mixture is heated at 120° C. for 22 hours. After standing, the mixture is filtered. The solid is dissolved in 150 ml of ethanol-water (9:1) and 10 g of potassium hydroxide is added. The mixture is refluxed for 6 hours, acidified with concentrated hydrochloric acid, diluted with water, filtered and the solid washed with water to give crystals. The crystals ae dissolved in aqueous sodium hydroxide and the solution extracted once with chloroform and once with ether. The aqueous layer is acidified with concentrated hydrochloric acid and the mixture filtered. The solid is recrystallized from glacial acetic acid to give white crystals, mp 134°-137° C.

Workup

  1. filtrationthe mixture is filtered
  2. dissolutionThe solid is dissolved in 150 ml of ethanol-water (9:1)
  3. addition10 g of potassium hydroxide is added
  4. temperatureThe mixture is refluxed for 6 hours
  5. additiondiluted with water
  6. filtrationfiltered
  7. washthe solid washed with water
  8. customto give crystals
  9. extractionthe solution extracted once with chloroform and once with ether
  10. filtrationthe mixture filtered
  11. customThe solid is recrystallized from glacial acetic acid
  12. customto give white crystals, mp 134°-137° C.

Sources & evidence

ORD record
ord-9f73402cae524ec68088409b298ee814
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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