Sulfuric Acid → 1-Methylethyl 2-hydroxy-5-(1-oxooctadecyl)benzoate

HRID 1381053Notes

Reaction equation

HRID 1381053 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH:35](O)([CH3:37])[CH3:36]>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:7][C:3]=1[C:4]([O:6][CH:35]([CH3:37])[CH3:36])=[O:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 51009112-Hydroxy-5-(1-oxooctadecyl)benzoic acid

Product 1

HCID 133934571-Methylethyl 2-hydroxy-5-(1-oxooctadecyl)benzoate

Procedure

A solution of the title product of Example 4 (6.2 mmole) and sulfuric acid (0.5 ml) in 120 ml of isopropyl alcohol (100 ml) was heated at 45° C. for 12 days, refluxed for 36 hours, and concentrated on a rotary evaporator to an oil. The oil was dissolved in methylene chloride, washed with water, dried over sodium sulfate, filtered, and concentrated under vacuum to give the title compound, m.p. 72°-73° C.

Workup

  1. temperaturerefluxed for 36 hours
  2. concentrationconcentrated on a rotary evaporator to an oil
  3. dissolutionThe oil was dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c2928938136e427eba6847e0bf726e60
Source dataset
uspto-grants-1986_04
Patent number
US04584397

Reaction notes

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