Acetic Acid → HCID 20250616, compound

HRID 1284882Notes

Reaction equation

HRID 1284882 reaction equation
[CH2:1]([C:16]1C(=O)[C:18]2[C:23]([C:24](=[O:26])[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:28]=[O:29].[BrH:30].[C:31](O)(=O)C>>[Br:30][CH2:31][C:25]1[C:24](=[O:26])[C:23]2[C:22]([C:28](=[O:29])[C:16]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 13234999HCID 13234999, compound

Product 1

HCID 20250616HCID 20250616, compound

Procedure

2-Pentadecyl-1,4-naphthoquinone (60 g, 0.163 mol) was suspended in acetic acid (2 l) with stirring. Aqueous 37 percent formaldehyde (200 ml, 2.4 mol) and 31 percent hydrogen bromide in acetic acid (660 ml, 2.4 mol) were added and the mixture was stirred at room temperature overnight. The precipitated product was then filtered off, washed with a minimum amount of acetic acid, water, and was then air dried. Yield: 60 g (80 percent). (Method of R. H. Thomson, J. Chem. Soc., 1953, 1196).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationThe precipitated product was then filtered off
  3. washwashed with a minimum amount of acetic acid, water
  4. customair dried

Sources & evidence

ORD record
ord-e1cbd8ba9ef84f109af43bada092c574
Source dataset
uspto-grants-1986_01
Patent number
US04564577

Reaction notes

Loading…