Hydrochloric Acid → HCID 53701824, compound

HRID 1976303Notes

Reaction equation

HRID 1976303 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([CH3:20])[C:12]([CH3:19])=[CH:13][C:14]=2[CH3:18])[O:9]1.Br[CH2:25][C:26]([O:28][CH2:29]C)=[O:27].[OH-].[Na+].Cl>C1COCC1.O.CO>[CH3:7][C:8]1([CH2:21][CH2:22][O:23][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([CH3:20])[C:12]([CH3:19])=[CH:13][C:14]=2[CH3:18])[O:9]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetate2×HCID 14798Sodium HydroxideHCID 22000907HCID 22000907, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 53701824HCID 53701824, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
52.5 °C

Procedure

A solution of potassium tert-butoxide (1.92 g) in THF (10 ml) was added dropwise to a solution of 2-(2,5,7,8-tetramethylchroman-2-yl)ethanol (4.00 g) and ethyl bromoacetate (2.00 ml) in THF (20 ml) at 0-10° C. and the mixture was stirred for 30 minutes under same condition. After addition of ethyl bromoacetate (1.90 ml), a solution of potassium tert-butoxide (1.92 g) in THF (10 ml) was added dropwise and the mixture was stirred at 0-10° C. for 30 minutes. This procedure was repeated 3 times. A solution of NaOH (5.0 g) in water (10 ml) was added and heated at 50-55° C. for 5 hours. The mixture was adjusted to pH 3 with 6N hydrochloric acid (6N HCl) and extracted with AcOEt. The organic phase was dried over MgSO4 and concentrated under reduced pressure to give a syrup. A mixture of the syrup and a cation-exchange resin, Amberlyst® 15 (1 g) in MeOH (100 ml) was heated under reflux for 30 hours. After removal of catalyst, the solution was concentrated under reduced pressure to give a syrup. The syrup was purified by chromatography over silica gel (AcOEt-hexane 5:95) to give methyl [2-(2,5,7,8-tetramethylchroman-2-yl)ethoxy]acetate as an oil (3.37 g).

Workup

  1. stirringthe mixture was stirred at 0-10° C. for 30 minutes
  2. extractionextracted with AcOEt
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. additionA mixture of the syrup
  7. temperatureunder reflux for 30 hours
  8. customAfter removal of catalyst
  9. concentrationthe solution was concentrated under reduced pressure
  10. customto give a syrup
  11. customThe syrup was purified by chromatography over silica gel (AcOEt-hexane 5:95)

Sources & evidence

ORD record
ord-86ca24c3bedf48bd800bdea12797a601
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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