Water → HCID 19847612, compound

HRID 2350864Notes

Reaction equation

HRID 2350864 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:23]1([CH3:32])[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=1Cl.O>C(OCC)C>[C:23]1([CH3:32])[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 154622-Chloro-1,3,5-trimethylbenzeneHCID 14603109Methyl 4-(4-hydroxybutyl)benzoate

Product 1

HCID 19847612HCID 19847612, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 65.07 g (1.0 eq) of methyl 4-(4-hydroxybutyl)benzoate and 33.20 (1.05 eq) of triethylamine in 350 mL of anhydrous ethyl ether, stirred under nitrogen and cooled to 0° C., are added in a dropwise fashion, 37.58 g (1.05 eq) of mesityl chloride. A solid forms and the reaction mixture is gradually brought to room temperature and stirred under nitrogen for 4 hours. Four hundred milliliters of water are then added and the organic layer is separated, washed with water, dried over magnesium sulfate, and concentrated to yield methyl 4-(4-mesitylbutyl)benzoate, m.p. 52°-53° C.; IR (KBr) vmax 3010, 2930, 2850, 1700, 1603, 1432, 1334, 1323, 1165, 1104, 937, 822, and 700 cm-1 ; 1H NMR (CDCl3) delta 7.92 (d, J=8.2 Hz, 2H, Ar), 7.22 (d, J=8.2 Hz, 2H, Ar), 4.18-4.22 (m, 2H, CH2OMs), 3.86 (s, 3H OCH3), 2.96 (s, 3H, SO2CH3), 2.65-2.68 (m, 2H, benzyl), 1.72-1.74 (m, 4H, 2° aliphatic).

Workup

  1. customis gradually brought to room temperature
  2. stirringstirred under nitrogen for 4 hours
  3. customthe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f3f8f82365149ec9fa8d4f90e72d68a
Source dataset
uspto-grants-1989_10
Patent number
US04871743

Reaction notes

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