Phloroglucinol → HCID 57560093, compound

HRID 1724114Notes

Reaction equation

HRID 1724114 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]([OH:8])=[CH:3][C:2]=1[OH:9].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:10]([O:7][C:6]1[CH:5]=[C:4]([OH:8])[CH:3]=[C:2]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:1]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 359PhloroglucinolHCID 81741-Decanol

Product 1

HCID 57560093HCID 57560093, compoundYield 37%

Conditions

Temperature
70 °C

Procedure

Into a suspension of phloroglucin 8 (5.00 g, 39.7 mmol) in 1-decanol (80 ml) dry gaseous HCl is introduced for 40 min, and the orange/red mixture is subsequently heated to 70° C. for an additional 3.5 h. After finalization of the reaction, the excess 1-decanol is distilled off in vacuo, and the residue of the reaction is purified by means of column chromatography (silica gel, CH2Cl2). 5.92 g (37%) of compound 9 are obtained as a colorless solid. Melting point: 48-50° C.; IR (KBr) 3340, 2880, 2810 cm−1; 1H-NMR (CDCl3) δ 6.06 (t, 2.1 Hz, 1H), 5.99 (d, 2.1 Hz, 2H), 4.80 (s, 1H, OH), 3.89 (t, 6.7 Hz, 4H), 1.80-1.69 (m, 4H), 1.48-1.23 (m, 28H), 0.88 (t, 6.8 Hz, 6H); MS (FD) m/z 407 (M+). Anal. calc. for C26H46O3. C, 76.79; H, 11.40. Found C, 76.74; H, 11.44.

Workup

  1. additionis introduced for 40 min
  2. customAfter finalization of the reaction
  3. distillationthe excess 1-decanol is distilled off in vacuo
  4. customthe residue of the reaction is purified by means of column chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-c8ed884bd05c4046892b68db8dba7344
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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