Hydrochloric Acid → (2-(Benzyloxy)-5-(tert-butyl)phenyl)methanol

HRID 2401651Notes

Reaction equation

HRID 2401651 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 547951252-(Benzyloxy)-5-(tert-butyl)benzaldehyde

Product 1

HCID 59544156(2-(Benzyloxy)-5-(tert-butyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a stirred suspension of compound 3 (974 g, 3.63 mol) in MeOH (4000 mL) was slowly added NaBH4 (121 g, 3.20 mol) at 0-20° C. The solution was left stirring at 15° C. for 3 hours, and then cooled to 0° C. 2N HCl (aq) (1300 mL) was added dropwise at below 20° C. The solution was then filtered and evaporated to dryness, and the residue was dissolved in MTBE (5 L). The solution was then washed with water (2 L×2) and brine (1.5 L×1). Evaporation of the solvent gave compound 4 as a light-yellow solid which was used in the next reaction without further purification. 1H NMR (DMSO-d6; 400 MHz) δ 7.40 (m), δ 7.32 (m), δ 7.17 (m), δ 6.91 (m), δ 5.09 (s), δ 5.00 (t), δ 4.56 (d), δ 1.26 (s).

Workup

  1. customat 0-20° C
  2. waitThe solution was left
  3. temperaturecooled to 0° C
  4. filtrationThe solution was then filtered
  5. customevaporated to dryness
  6. dissolutionthe residue was dissolved in MTBE (5 L)
  7. washThe solution was then washed with water (2 L×2) and brine (1.5 L×1)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cb4f9ead296c45b3946438cf19cca703
Source dataset
uspto-grants-2014_08
Patent number
US08796308B2

Reaction notes

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