Phosphoric Acid → HCID 74020140, compound

HRID 1437836Notes

Reaction equation

HRID 1437836 reaction equation
[Cl:1][C:2]1[C:3]([OH:25])=[C:4]([CH:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].P(=O)(O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([OH:25])=[C:4]([CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 23134889HCID 23134889, compound

Product 1

HCID 74020140HCID 74020140, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (33 mg, 0.089 mmol) was stirred in acetic acid (2 ml) in the presence of 85% phosphoric acid (0.024 mmol) at a reflux temperature for 1.5 hours. The reaction mixture was cooled to room temperature. After extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (chloroform) to obtain 5-chloro-3-(1-dodecenyl)-2,4-dihydroxy-6-methylbenzaldehyde (24 mg, yield 76%).

Workup

  1. customAfter extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (chloroform)

Sources & evidence

ORD record
ord-77d53120d5eb4e29811c92ee2df0ed71
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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