O-Xylene → HCID 21408027, compound

HRID 2072322Notes

Reaction equation

HRID 2072322 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Na].C1(C)C(C)=CC=CC=1.Br[C:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:31])[CH2:29][OH:30]>C(O)C>[S:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([CH3:31])[CH2:29][OH:30])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 7237O-Xylene2×HCID 5360545SodiumHCID 10633937HCID 10633937, compoundHCID 21407997HCID 21407997, compound

Product 1

HCID 21408027HCID 21408027, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2.42 g. of 4p-hydroxyphenyl-thiochromane and 0.23 g. of sodium in 50 ml. of xylene is boiled for 3 hours. The mixture is allowed to cool to 20° C., 2.15 g. of 2-bromo-2-phenylpropanol in 10 ml. of xylene are added and the suspension is stirred for 6 hours at the boil, cooled and treated with 2 ml. of ethanol. The inorganic precipitate is filtered off, the filtrate is evaporated, the residue is taken up in ether and the solution is washed with NaHCO3 solution and saturated NaCl solution, dried over MgSO4 and evaporated, to give 2-[4-(4-thiochromanyl)-phenoxy]-2-phenylpropanol, nD20 1.6172.

Workup

  1. additionA mixture of 2.42 g
  2. temperaturecooled
  3. additiontreated with 2 ml
  4. filtrationThe inorganic precipitate is filtered off
  5. customthe filtrate is evaporated
  6. washthe solution is washed with NaHCO3 solution and saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-2270e135dc74439ab522449db3e0fe2d
Source dataset
uspto-grants-1977_09
Patent number
US04051173

Reaction notes

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