Phenol → (2,2-Diethoxyethoxy)benzene

HRID 1609704

Reaction equation

HRID 1609704 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11]>CN1C(=O)N(C)CCC1>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 96328(2,2-Diethoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
110 °C

Procedure

Sodium hydride (5.83 g of a 55% dispersion in mineral oil) was added to a solution of phenol (12.56 g) in DMPU (25 ml) at 5° C. and the mixture was stirred for 30 minutes. Bromoacetaldehyde diethyl acetal (10.05 ml) was added and the mixture was heated at 110° C. for 5 hours, then allowed to cool. The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml) and the organic phase was separated and washed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml). The aqueous fractions were combined and re-extracted with ethyl acetate (100 ml). The combined organic extracts were dried (MgSO4) and concentrated. The resultant oil was purified by flash column chromatography, eluting with ethyl acetate/hexane (1:10 v/v) to give 2-phenoxyacetaldehyde diethyl acetal (9.43 g) as an oil; NMR: 1.25(6H,t, J=7.0 Hz), 3.6-3.85(4H,m), 4.05(2 H,d, J=6.0 Hz), 4.85 (1H,t, J=6.0 Hz) and 6.9-7.35(5H,m).

Workup

  1. temperatureto cool
  2. customThe mixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. customthe organic phase was separated
  4. washwashed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml)
  5. extractionre-extracted with ethyl acetate (100 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe resultant oil was purified by flash column chromatography
  9. washeluting with ethyl acetate/hexane (1:10 v/v)

Sources & evidence

ORD record
ord-c2616766ac3d4775bb739add6494f839
Source dataset
uspto-grants-1995_03
Patent number
US05401849

Linked notes

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