Hydrochloric Acid → 4-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

HRID 652019Notes

Reaction equation

HRID 652019 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=1.[OH-].[K+].C(O)C.Cl>O>[CH3:30][Si:2]([CH3:1])([CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 13884860Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Product 1

HCID 138848624-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 14.1 g. ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate and 6.4 g. 85% potassium hydroxide in 150 ml. 95% ethanol was heated at 75° for 5 hr. The reaction was diluted with 300 ml. water and adjusted to pH 3.5 with concentrated hydrochloric acid. The precipitate was filtered, dried, and crystallized from acetone to yield a white solid, m.p. 105°-107° C.

Workup

  1. additionThe reaction was diluted with 300 ml
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customcrystallized from acetone
  5. customto yield a white solid, m.p. 105°-107° C.

Sources & evidence

ORD record
ord-d088aad4a46649af92cda19413d9306d
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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