Carbon Tetrachloride → HCID 53642312, compound

HRID 236658Notes

Reaction equation

HRID 236658 reaction equation
[CH3:1][C@@:2]1([CH2:16][CH2:17]O)[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>>[CH3:1][C@@:2]1([CH2:16][CH2:17][Cl:39])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 642448HCID 642448, compound

Product 1

HCID 53642312HCID 53642312, compoundYield 79.2%

Procedure

A mixture of 2 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-hydroxyethyl)-chroman, 8 g of carbon tetrachloride and 2.6 g of triphenylphosphine was refluxed for 3 hours, after which the reaction mixture was allowed to cool, the precipitate formed was filtered off under suction and the filtrate was chromatographed over silica gel, using a 5:1 hexane/acetone solvent mixture. 1.7 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-chloroethyl)-chroman were obtained. [α]D20 =-9.1° (c=2, chloroform), mp.=111° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureto cool
  3. customthe precipitate formed
  4. filtrationwas filtered off under suction
  5. customthe filtrate was chromatographed over silica gel

Sources & evidence

ORD record
ord-17c84253594f4099b278cbeaea646e01
Source dataset
uspto-grants-1987_02
Patent number
US04645845

Reaction notes

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