Hydrochloric Acid → HCID 20088775, compound

HRID 275536Notes

Reaction equation

HRID 275536 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])[CH3:5].Cl>CCO>[CH3:17][C:14]([C:11]1[CH:10]=[C:9]([CH:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[OH:19])[CH:8]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[C:12]=1[OH:13])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1898376Methanone, [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenyl-HCID 4311764Sodium borohydride

Product 1

HCID 20088775HCID 20088775, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Over a 25-minute period NaBH4 (1.89 g, 0.05 mole) is added to a solution of 3.1 g (0.01 mole) of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenylmethanone (C. D. Cook, JOC, 1960, p. 1429) in 50 mL absolute EtOH while maintaining the temperature at 10°-15° C. The reaction mixture is then allowed to come to room temperature for 1.5 hours. The reaction mixture is cooled to 0° and 4N HCl (12 mL) is slowly added. The white precipitate is filtered off and washed with H2. It is taken up in Et2O and washed with saturated NaHCO3. After drying over Na2SO4 the Et2O is evaporated to dryness yielding an analytically pure olive-colored product, 2.9 g (93%), m.p. 117°-119° C.

Workup

  1. temperaturewhile maintaining the temperature at 10°-15° C
  2. temperatureThe reaction mixture is cooled to 0°
  3. filtrationThe white precipitate is filtered off
  4. washwashed with H2
  5. washwashed with saturated NaHCO3
  6. dry with materialAfter drying over Na2SO4 the Et2O
  7. customis evaporated to dryness
  8. customyielding an analytically pure olive-colored product, 2.9 g (93%), m.p. 117°-119° C.

Sources & evidence

ORD record
ord-7c84488b7f504cfbbfef1a0914e732d4
Source dataset
uspto-grants-1995_02
Patent number
US05393923

Reaction notes

Loading…