Hydrochloric Acid → 2-[4-(Dodecyloxy)phenoxy]butanoyl chloride

HRID 1759587Notes

Reaction equation

HRID 1759587 reaction equation
[CH2:1]([O:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH2:23][CH3:24])[C:20](O)=[O:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC1(C)C2C(=CC(O)=CC=2)C(C)(C)C1.C[O-].[Na+].COC(=O)C(Br)CC.[Na].[OH-].[Na+].[ClH:55]>CO.C(O)(C)C.C1(C)C=CC=CC=1>[CH2:1]([O:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH2:23][CH3:24])[C:20]([Cl:55])=[O:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 95577Butanoic acid, 2-bromo-, methyl esterHCID 1045671,1,3,3-Tetramethylindan-5-ol2×HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 20531327HCID 20531327, compound

Product 1

HCID 205313182-[4-(Dodecyloxy)phenoxy]butanoyl chloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

In the same way as in the case of 2-(4-n-dodecyloxyphenoxy)-butyric acid all of the methanol was distilled off from a mixture of 89 g (0.468 mole) of 1,1,3,3-tetramethyl-5-indanol, 750 ml of anhydrous toluene, and 86.7 ml (0.468 mole) of a 30% solution of sodium methanolate in methanol. 93.2 g (0.515 mole) of α-bromobutyric acid methyl ester were added to the suspension of the resulting sodium salt of 1,1,3,3-tetramethyl-5-indanol. The mixture was refluxed for 7 hours. 180 ml of isopropanol and 140 ml of 5 N sodium hydroxide were added to the hot (80° C.) mixture and refluxing was then continued for 1 hour. The mixture was cooled down to room temperature and admixed with 164 ml of 5 N hydrochloric acid. The toluene layer was decanted. The residue was dried and the solvent was evaporated.

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. temperaturerefluxing
  3. customThe toluene layer was decanted
  4. customThe residue was dried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-05df3e572f054918bdc6327a329a833d
Source dataset
uspto-grants-1982_07
Patent number
US04341864

Reaction notes

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