gamma-Propanol → 4-(3-Hyd-roxypropyl)-2-t-butylphenol

HRID 1170064Notes

Reaction equation

HRID 1170064 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH2:18][OH:19])[CH:8]=[C:9](C(C)(C)C)[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH2:18][OH:19])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 169766gamma-Propanol

Product 1

HCID 134050654-(3-Hyd-roxypropyl)-2-t-butylphenolYield 76.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A stirred solution of III (12.5 Kg) in trifluoroacetic acid (60.0 L) was heated 40° C. for 6 hrs. After completion of reaction on TLC, reaction mixture was quenched in ice-water and extracted 3 times with dichloromethane (25.0 L). Total organic layers were combined and evaporated to dryness at atmospheric pressure. A solution of sodium hydroxide (3.0 Kg) in methanol (50.0 L) was added to the residue and stirred at room temperature for 1 hr. The solution was neutralized with 1N HCl and extracted 3 times with dichloromethane (25.0 L). All the organic layers were combined and washed with saturated sodium carbonate solution (10.0 L), DM Water (10.0 L), brine (10.0 L) and evaporated to dryness under reduced pressure to give the title compound (7.5 Kg)

Workup

  1. customAfter completion of reaction
  2. customon TLC, reaction mixture
  3. customwas quenched in ice-water
  4. extractionextracted 3 times with dichloromethane (25.0 L)
  5. customevaporated to dryness at atmospheric pressure
  6. additionA solution of sodium hydroxide (3.0 Kg) in methanol (50.0 L) was added to the residue
  7. extractionextracted 3 times with dichloromethane (25.0 L)
  8. washwashed with saturated sodium carbonate solution (10.0 L), DM Water (10.0 L), brine (10.0 L)
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ebba5e16d5fc49b6b9e9838f05b3786e
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Reaction notes

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