4-Amino-m-cresol → HCID 66704166, compound

HRID 424822Notes

Reaction equation

HRID 424822 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.[CH:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([CH3:22])[CH:13]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:10][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([CH3:22])[CH:13]=2)=[C:3]([CH3:9])[CH:4]=1

Participants

5

Reactant 3

HCID 178194-Amino-m-cresolHCID 5049666Sodium triacetoxyborohydrideHCID 20134203Methyl 4-formyl-2-methylbenzoate

Product 1

HCID 66704166HCID 66704166, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Amino-m-cresol (242 g, 1.96 mol) is added to a slurry of 4-formyl-2-methyl-benzoic acid, methyl ester (350 g, 1.96 mol) and acetic acid (3100 mL) at room temperature. Sodium triacetoxyborohydride (728 g, 3.44 mol) is added portionwise, keeping the temperature below 30° C. using an ice water bath. After overnight stirring, the reaction mixture is concentrated under reduced pressure. The residue is adjusted to pH 5 using aqueous saturated sodium bicarbonate. The resulting solid is filtered off, washed with water, and dried under vacuum overnight to give the title compound (460 g, 82%) as a brown powder. ES/MS m/e 179 (M+1).

Workup

  1. customthe temperature below 30° C.
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. filtrationThe resulting solid is filtered off
  4. washwashed with water
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-1d6e1b9c8bfd4f048ab5370404cf3721
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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