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Water → 4-Octyloxycarbonyloxybenzoic acid 4-(1-methylheptyloxycarbonyl)phenyl ester

HRID 1194647
Notes
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Reaction equation

HRID 1194647 reaction equation
[CH3:1][CH:2]([O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:19]([O:27][C:28]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:1][CH:2]([O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:35](=[O:36])[C:34]2[CH:38]=[CH:39][C:31]([O:30][C:28]([O:27][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:29])=[CH:32][CH:33]=2)=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 110103794-(1-Methylheptyloxycarbonyl)phenolHCID 137419804-(Chlorocarbonyl)phenyl octyl carbonate

Product 1

HCID 540222914-Octyloxycarbonyloxybenzoic acid 4-(1-methylheptyloxycarbonyl)phenyl esterYield 28.2%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

Optically active 4-(1-methylheptyloxycarbonyl)phenol (10 g, 0.04 mol) was dissolved in pyridine (70 ml), followed by dropwise adding to the solution, under cooling, 4-octyloxycarbonyloxybenzoic chloride (11.4 g, 0.035 mol) prepared in the same manner as in the paragraph (ii) of Example 1, agitating the mixture at 50°-60° C. for 2 hours, placing water and toluene in the reaction solution after completion of the reaction, sufficiently agitating the mixture, washing the separated toluene layer with 6N--HCl, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the resulting toluene layer with anhydrous sodium sulfate, distilling off toluene to obtain a raw objective product, and recrystallizing this product from ethanol to obtain optically active 4-octyloxycarbonyloxybenzoic acid 4-(1-methylheptyloxycarbonyl)phenyl ester (5.2 g), which exhibited no liquid crystal phase and had a m.p. of 33.0° C. Further, by replacing octyl chloroformate used, by other alkyl chloroformates, various optically active 4-alkyloxycarbonyloxybenzoic acid 4-(1-methyl-heptyloxycarbonyl)phenyl esters are obtained. The phase transition points thereof are shown in Tables 1 and 2.

Workup

  1. additionby dropwise adding to the solution
  2. temperatureunder cooling
  3. customafter completion of the reaction
  4. stirringsufficiently agitating the mixture
  5. washwashing the separated toluene layer with 6N
  6. dry with materialdrying the resulting toluene layer with anhydrous sodium sulfate
  7. distillationdistilling off toluene
  8. customto obtain a raw objective product
  9. customrecrystallizing this product from ethanol

Sources & evidence

ORD record
ord-6ea86f9223ed4a36b6896e40fba7e2dd
Source dataset
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04816181

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes