2-Methylbenzenesulfonic acid → HCID 59473766, compound

HRID 2069711Notes

Reaction equation

HRID 2069711 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([F:13])[CH:12]=1)C=O)([CH3:4])([CH3:3])[CH3:2].C1(C)C(S(O)(=O)=O)=CC=CC=1.C(N(CC)CC)C.[CH:32](OC)([O:35][CH3:36])[O:33][CH3:34]>CO>[C:1]([C:5]1[CH:12]=[C:11]([F:13])[CH:10]=[C:7]([CH:32]([O:35][CH3:36])[O:33][CH3:34])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 59473813HCID 59473813, compound

Product 1

HCID 59473766HCID 59473766, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-tert-Butyl-5-fluoro-benzaldehyde (252 g, 1.4 moles) was dissolved in methanol (4 vol, 1000 ml) and trimethyl orthoformate (1 vol, 252 ml). Toluenesulfonic acid (3.4% w/w, 6 g) was added in one portion and the resulting solution stirred at rt for 1 hour. Triethylamine (0.12 vol, 30 mL) was added and the reaction concentrated to an oil, and then re-suspended in ethyl acetate (3 L) and NaHCO3 (aq. sat., 1 L) and water (1 L) with vigorous mixing. The organic phase was washed with additional water (1 L), polish filtered and then concentrated to provide an orange oil (311.2 g, 98.5%), used directly in the next reaction.

Workup

  1. concentrationthe reaction concentrated to an oil
  2. washThe organic phase was washed with additional water (1 L)
  3. filtrationpolish filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-56f7df7b57cf45c78c911c4d348b41c8
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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