4-tert-Butyl-3-methoxybenzoic acid → 1206775-43-0

HRID 1517528Notes

Reaction equation

HRID 1517528 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 127397584-tert-Butyl-3-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 534014571206775-43-0Yield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Preparation of 26—To a solution of 4-tert-butyl-3-methoxy-benzoic acid (3 g, 14.4 mmol, CASRN 79822-46-1) and THF (60 mL) cooled to 0° C. was added a solution of LiAlH4 in THF (29 mL, 28.8 mmol, 1M THF solution). The reaction was stirred overnight at RT then quenched by dropwise addition of aqueous THF (1.1 mL of water in 10 mL of THF) followed by 1.1 mL of 15% NaOH and then 3.3 mL of water. The reaction was stirred for 1 h then solid Na2SO4 was added and the resulting suspension stirred overnight, filtered through a pad of CELITE, and evaporated to afford 2.8 g of 4-tert-butyl-3-methoxy-benzyl alcohol.

Workup

  1. customthen quenched by dropwise addition of aqueous THF (1.1 mL of water in 10 mL of THF)
  2. stirringThe reaction was stirred for 1 h
  3. additionsolid Na2SO4 was added
  4. stirringthe resulting suspension stirred overnight
  5. filtrationfiltered through a pad of CELITE
  6. customevaporated

Sources & evidence

ORD record
ord-b7106af81a554c499723c24c022eb1be
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

Loading…