1,2-Dichloroethane → HCID 22134862, compound

HRID 328863Notes

Reaction equation

HRID 328863 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:6][CH2:5]2.Cl[CH2:20][CH2:21]Cl.OS(O)(=O)=O>C(O)C>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([O:16][CH2:20][CH3:21])=[O:15])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 1118Sulfuric AcidHCID 40634Trolox

Product 1

HCID 22134862HCID 22134862, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25.0 g. of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, 100 ml. of 1,2-dichloroethane, 17.5 ml. of ethanol and 1.0 ml. of concentrated H2SO4 was heated at reflux under N2 for 20 hours. The dark mixture was washed with H2O, saturated sodium bicarbonate solution and brine, dried over sodium sulfate and stripped of solvent to give a light yellow solid. Crystallization from ether gave (±)-ethyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate, m.p. 124°-126° .

Workup

  1. additionA mixture of 25.0 g
  2. temperatureat reflux under N2 for 20 hours
  3. washThe dark mixture was washed with H2O, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customto give a light yellow solid
  6. customCrystallization from ether

Sources & evidence

ORD record
ord-3fac385ed5b84dca8c5b2597861455c5
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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