Hydrochloric Acid → HCID 14989157, compound

HRID 2082297Notes

Reaction equation

HRID 2082297 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[CH:21]([Mg]Cl)([CH3:23])[CH3:22].Cl.O>O1CCCC1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][CH:19]([OH:20])[CH:21]([CH3:23])[CH3:22])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 214746842,6-Bis(1,1-dimethylethyl)-4-[(3-hydroxypropyl)thio]phenolHCID 178418918HCID 178418918, compound

Product 1

HCID 14989157HCID 14989157, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio] propanol (2.0 g, prepared as described in U.S. Pat. No. 4,857,558) was dissolved in 20 ml of dry tetrahydrofuran under argon and added to 8.5 ml of 2 M isopropylmagnesium chloride in tetrahydrofuran that had previously been added under argon gas to a flask that had been dried in vacuo overnight. Reaction temperature was maintained at 10°-15° C. with an ice bath. When addition was complete, the reaction mixture was allowed warm to room temperature and stirred for 3 hours. 2N hydrochloric acid (2 ml) was added followed by 50 ml of water and the mixture extracted with ethyl acetate three times. The organic extracts were combined, washed with water twice and dried over sodium sulfate. The solvent was removed in vacuo after filtration and the crude product chromatographed on silica to give the title compound.

Workup

  1. additionhad previously been added under argon gas to a flask that
  2. customhad been dried in vacuo overnight
  3. customReaction temperature
  4. temperaturewas maintained at 10°-15° C. with an ice bath
  5. additionWhen addition
  6. extractionthe mixture extracted with ethyl acetate three times
  7. washwashed with water twice
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed in vacuo
  10. filtrationafter filtration
  11. customthe crude product chromatographed on silica

Sources & evidence

ORD record
ord-5c3913691fa442aa961adbc9b02fbac4
Source dataset
uspto-grants-1993_02
Patent number
US05189038

Reaction notes

Loading…