5-Amino-2-hydroxytoluene → HCID 14500509, compound

HRID 1762881Notes

Reaction equation

HRID 1762881 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>CC(C)=O>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1)=[O:17]

Participants

4

Reactant 2

HCID 760815-Amino-2-hydroxytolueneHCID 898486-Bromohexanoyl chloride

Product 1

HCID 14500509HCID 14500509, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 25 g (0.20 mol) of 4-amino-2-methylphenol in about 450 mL of acetone was stirred at room temperature and 20.6 g (0.09 mol) of 6-bromohexanoyl chloride was dripped in over 20 minutes. The reaction was stirred at room temperature for 3 hours then ice-cooled and filtered. The filtrate was stripped in vacuo to a residual oil which was triturated once in 225 mL of 1N HCl and then several times in cold water. The resulting gum was dissolved in absolute ethanol and 28 g of product (95%) were crystallized out by the addition of water, mp 111°-112° C. The product, which contained a small amount of 4-amino-2-methylphenol, was used as is in the following reaction.

Workup

  1. customwas dripped in over 20 minutes
  2. temperatureice-cooled
  3. filtrationfiltered
  4. customwas triturated once in 225 mL of 1N HCl
  5. dissolutionThe resulting gum was dissolved in absolute ethanol
  6. custom28 g of product (95%) were crystallized out by the addition of water, mp 111°-112° C
  7. customas is in the following reaction

Sources & evidence

ORD record
ord-0554a6fb236749169e68edcde92b7f10
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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