Carbon Dioxide → HCID 59473800, compound

HRID 2069712Notes

Reaction equation

HRID 2069712 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:17](=[O:19])=[O:18].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:17]([OH:19])=[O:18])=[C:7]([CH:12]([O:13][CH3:14])[O:15][CH3:16])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 313Hydrochloric AcidHCID 59473766HCID 59473766, compound

Product 1

HCID 59473800HCID 59473800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

1-tert-Butyl-3-dimethoxymethyl-5-fluoro-benzene (333 g, 1.47 moles) was dissolved in THF (10 vol, 3.3 L) and cooled to −70° C. secBuLi (1.4M in cyclohexanes, 1.0 eq, 1000 mL) was added drop-wise over 1.5 hours. The solution was stirred at −70° C. for one hour and then CO2 gas was added to the reaction via a sintered glass gas dispersion tube, while maintaining vigorous stirring. The reaction was allowed to warm with vigorous stirring with adequate venting for release of excess CO2 from the solution. Once the internal temperature had reached +10° C. the reaction was quenched with water (3 L) followed by conc. HCl (1.15 eq, 140 mL). The aqueous fraction was extracted to ethyl acetate (1 L) and the combined organic fractions were combined and washed with water (2×1 L), and then concentrated with solvent replacement with heptanes. The resulting fine crystals were filtered, washed with heptanes and then dried at room temperature under vacuum with N2 sweep to provide 220.3 g (55.3%).

Workup

  1. additionwas added drop-wise over 1.5 hours
  2. temperaturewhile maintaining vigorous stirring
  3. temperatureto warm
  4. customhad reached +10° C.
  5. customwas quenched with water (3 L)
  6. extractionThe aqueous fraction was extracted to ethyl acetate (1 L)
  7. washwashed with water (2×1 L)
  8. concentrationconcentrated with solvent replacement with heptanes
  9. filtrationThe resulting fine crystals were filtered
  10. washwashed with heptanes
  11. dry with materialdried at room temperature under vacuum with N2 sweep
  12. customto provide 220.3 g (55.3%)

Sources & evidence

ORD record
ord-858054f2779547529a2ffe94fc061d99
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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