Hydrochloric Acid → HCID 15745027, compound

HRID 1587467Notes

Reaction equation

HRID 1587467 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1.O1CCCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C(C(C)=O)C(C)C.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 170289Benzeneacetic acid, 4-hydroxy-.alpha.-(4-hydroxyphenyl)-HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15745027HCID 15745027, compoundYield 106.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a 2-liter Morton flask equipped with a mechanical stirrer and a half-moon paddle is charged 30.50 g (0.125 mole) of 2,2-bis(4-hydroxyphenyl)acetic acid and 1 L of tetrahydrofuran (THF) under a nitrogen atmosphere. LiAlH4 (18.9 g, 0.5 mole) is added with stirring to the reaction mixture over a period of six days. The reaction temperature is about 25° C. at the outset and is increased to 65° C. after one day and maintained at that temperature throughout the remaining five days of the addition of the LiAlH4. After a total of 12.5 days, the reaction mixture is cooled to 0° C. and 100 mL of water is added dropwise to the reaction mixture. The pH of reaction mixture is lowered to a pH of 1 by the addition of 10 percent HCl and the resulting phases are separated. The organic phase is evaporated to form a solid and the solid is dissolved in 500 mL of methyl isobutyl ketone. After washing the resulting solution with 100 mL of an aqueous solution of 5 percent NaHCO3, the solution is concentrated in vacuo to yield 30.7 g of 2,2-bis(4-hydroxyphenyl)ethanol as an orange gum. This gum is recrystallized from 430 mL of water to yield 23.0 g of a light brown solid. Upon vacuum drying at 100° C., the solid melted and lost weight to 21.1 g (yield of 73 percent) which weight loss corresponds to one molar equivalent of water.

Workup

  1. customTo a 2-liter Morton flask equipped with a mechanical stirrer
  2. customis about 25° C. at the outset
  3. temperatureAfter a total of 12.5 days, the reaction mixture is cooled to 0° C.
  4. customThe pH of reaction mixture
  5. customthe resulting phases are separated
  6. customThe organic phase is evaporated
  7. customto form a solid
  8. washAfter washing the resulting solution with 100 mL of an aqueous solution of 5 percent NaHCO3
  9. concentrationthe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-d8223f3ed0bf4d278c64cc3d4d05e4e6
Source dataset
uspto-grants-1993_06
Patent number
US05218075

Reaction notes

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