Hydrochloric Acid → HCID 19779197, compound

HRID 2081958Notes

Reaction equation

HRID 2081958 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:24])[C:12]2[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=2[O:10][C:9]1=[O:23].C(OCC)(=O)C.Cl>C(OCC)C.O>[CH3:20][C:17]([C:16]1[CH:15]=[C:14]([O:21][CH3:22])[CH:13]=[C:12]([C:8]([CH3:24])([CH3:7])[CH2:9][OH:23])[C:11]=1[OH:10])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 19779200HCID 19779200, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19779197HCID 19779197, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In 500 ml of diethyl ether was suspended 18 g of lithium aluminum hydride followed by addition of a solution of 3,3-dimethyl-7-(1,1-dimethylethyl)-5-methoxy-2(3H)-benzofuranone (104 g) in diethyl ether (400 ml) over a period of 1 hour with stirring at ambient temperature. The mixture was further stirred at ambient temperature for 1 hour. The reaction mixture was held under cooling in an ice bath and 60 ml of ethyl acetate, 100 ml of water and 900 ml of 10% hydrochloric acid were successively added. After phase separation, the aqueous layer was extracted with ethyl acetate and the organic layers were pooled, washed with saturated aqueous, sodium chloride solution, dried over magnesium sulfate and concentrated. The resultant crude product was crystallized from hexane to give 100 g of 2-(1,1-dimethylethyl)-6-(1,1-dimethyl-2-hydroxyethyl)-4-methoxyphenol as colorless crystals.

Workup

  1. stirringThe mixture was further stirred at ambient temperature for 1 hour
  2. temperatureunder cooling in an ice bath
  3. customAfter phase separation
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with saturated aqueous, sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe resultant crude product was crystallized from hexane

Sources & evidence

ORD record
ord-ff280b46164c451bbf8f29aa4c846da9
Source dataset
uspto-grants-1993_02
Patent number
US05187161

Reaction notes

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