Potassium Carbonate → HCID 13313585, compound

HRID 580973Notes

Reaction equation

HRID 580973 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].C1(C(C2[C:19]([CH2:20][O:21][CH2:22][C:23]3[C:28](C4C(=CC=C(O)C=4)O)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=[CH:16][CH:15]=2)=CC(=CC=1)O)O.C(=O)([O-])[O-:38].[K+].[K+]>CN(C)C=O>[CH2:22]([O:21][C:20]1[CH:15]=[CH:16][C:17]([O:38][CH2:2][CH2:3][O:4][CH3:5])=[CH:18][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 13313585HCID 13313585, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Bromoethylmethyl ether (105.7 g) was added to a stirred suspension of hydroquinone monobenzylether and unhydrous potassium carbonate (84.5 g) in N,N-dimethylformamide (250 ml). The reaction mixture was heated at 90° C. for 18 hours. The reaction mixture was allowed to cool to ambient temperature and the mixture filtered. The filtrate was dissolved in water (750 ml) and the aqueous mixture was extracted with ethyl acetate (5×150 ml). The ethyl acetate extracts were combined, washed with water (3×100 mls), brine (200 mls), dried (MgSO4) and evaporated to give 1-(benzyloxy)-4-(2-methoxyethoxy)benzene (102.4 g) as a solid; NMR: 3.3(3H,s), 3.61(2H,m), 4.0(2H,m), 5.02(2H,s), 6.9(4H,m) and 7.4(5H,m) and m/z 259(M+H).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationthe mixture filtered
  3. dissolutionThe filtrate was dissolved in water (750 ml)
  4. extractionthe aqueous mixture was extracted with ethyl acetate (5×150 ml)
  5. washwashed with water (3×100 mls), brine (200 mls)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-366b1591983a4f66bf2b0db3de78ad83
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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