Acetic Acid → HCID 13251037, compound

HRID 1649356Notes

Reaction equation

HRID 1649356 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][Si:15]([CH3:29])([CH3:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1)C.COCCO.[OH-].[K+].C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH3:29][Si:15]([CH3:28])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:14][CH2:13][CH2:12][NH:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 13251036HCID 13251036, compound

Product 1

HCID 13251037HCID 13251037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 11.50 g (26.5 mmol) of ethyl-4-(4,4-dimethyl-4-sila-n-hexadecylamino)-benzoate in 150 ml of freshly distilled 2-methoxy-ethanol (peroxide free) refluxing under nitrogen, is gradually added a solution of 10.0 g (approx. 161 mmol) of potassium hydroxide in 17 ml of water. After the addition, refluxing is continued for 45 mins. Then 15 ml (250 mmol) of acetic acid (100%) is added and the reaction mixture cooled. Toluene is then added and the mixture agitated. The organic phase is recovered, washed with 4 portions of water, dried over anh. sodium sulfate, filtered and the filtrate evaporated to yield crude title product as a semi-solid residue, which upon recrystallization from heptane-hexane (50/50) gives refined title product, m.p. (88)--89°-90°.

Workup

  1. additionAfter the addition
  2. temperaturerefluxing
  3. temperaturethe reaction mixture cooled
  4. customThe organic phase is recovered
  5. washwashed with 4 portions of water
  6. dry with materialdried over anh. sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. customto yield crude title product as a semi-solid residue, which
  10. customupon recrystallization from heptane-hexane (50/50)

Sources & evidence

ORD record
ord-196adfc5dbc74cf98fb4027deb3c6ef1
Source dataset
uspto-grants-1983_11
Patent number
US04416876

Reaction notes

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