p-Toluenesulfonic acid → Benzene, 1-(diethoxymethyl)-4-fluoro-

HRID 2228031Notes

Reaction equation

HRID 2228031 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([O:12][CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH3:11].[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[C:13]([O:12][CH2:10][CH3:11])(=[O:17])[CH3:20].[CH2:18]([O:17][CH:13]([O:14][CH2:15][CH3:16])[C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:19]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 31214Ethyl orthoformateHCID 680234-Fluorobenzaldehyde

Product 2

HCID 11788846Benzene, 1-(diethoxymethyl)-4-fluoro-Yield 71%HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluorobenzaldehyde, compound (5) (20 g, 17.3 ml, 161.15 mmol), triethylorthoformate (29.85 g, 33.5 ml, 201.43 mmol) and para-toluenesulphonic acid (0.28 g, 1.61 mmol ) in ethanol (100 ml) was stirred for 16 hours under a nitrogen atmosphere at ambient temperature. The mixture was treated with anhydrous sodium carbonate to pH 9, stirred for a further five minutes and then filtered and the filtrate evaporated to dryness. Purification by flash column chromatography eluting with iso-hexane/dichloromethane (1:1) and then with iso-hexane/ethyl acetate (9:1) gave a clear oil, compound (6)(22.77 g, 71% Yield).

Workup

  1. stirringstirred for a further five minutes
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. customPurification by flash column chromatography
  5. washeluting with iso-hexane/dichloromethane (1:1)

Sources & evidence

ORD record
ord-b2a5ed8c81ee4bc0ab3041affd70fa9b
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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