2-Thiocresol → HCID 66221073, compound

HRID 2111885Notes

Reaction equation

HRID 2111885 reaction equation
[CH3:1][C:2]1[C:7]([SH:8])=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br>CC(C)=O>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][S:8][C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 87122-ThiocresolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 66221073HCID 66221073, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of o-thiocresol (16.89 g, 136 mmol) in acetone (130 ml) is added potassium carbonate (20.5 g, 148 mmol) and a solution of bromoacetaldehyde dimethylacetal (19.93 g, 123 mmol) in acetone (20 ml) and the reaction mixture is stirred at ambient temperature overnight. The solids are filtered and washed with diethyl ether. The filtrate is concentrated and dissolved into ethyl acetate, washed successively with water, 0.5 N NaOH, and 2N NaOH. The combined aqueous fractions are extracted with dichloromethane. The combined organic fractions are dried over anhydrous MgSO4, filtered and concentrated to afford 1-[(2,2-dimethoxyethyl)thio]-2-methyl-benzene as a brown oil (23.4 g, 90%) that is used without further purification. 1H NMR (CDCl3): δ=7.33 (1H, brd), 7.19-7.08 (3H, m), 4.56 (1H, t), 3.38 (6H, s), 3.10 (2H, d), 2.42 (3H, s).

Workup

  1. filtrationThe solids are filtered
  2. washwashed with diethyl ether
  3. concentrationThe filtrate is concentrated
  4. dissolutiondissolved into ethyl acetate
  5. washwashed successively with water, 0.5 N NaOH, and 2N NaOH
  6. extractionThe combined aqueous fractions are extracted with dichloromethane
  7. dry with materialThe combined organic fractions are dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b574f027250c4b00925b5f62594a5159
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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