Hydrochloric Acid → 11-Phenoxyundecanoic acid

HRID 2051904Notes

Reaction equation

HRID 2051904 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].C[O-].[Na+].Cl>O.CN(C)P(N(C)C)(N(C)C)=O>[O:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 1781211-Bromoundecanoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 8159711-Phenoxyundecanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 9.4 g of phenol, 26.5 g of 11-bromoundecanoic acid and 250 ml of hexamethylphosphoramide chilled in an ice bath is added 10.5 g of sodium methoxide. A viscous mass developes and the mixture is stirred and heated at 100° C. for 20 hours. The mixture is diluted with cold water, acidified with concentrated hydrochloric acid, filtered and the solid washed with water to give gray crystals. Recrystallization from acetone gives pale gray crystals, mp 76°-78° C. A second crop of crystals is obtained from mother liquors, mp 75°-77° C.

Workup

  1. temperaturechilled in an ice bath
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customto give gray crystals
  5. customRecrystallization from acetone
  6. customgives pale gray crystals, mp 76°-78° C
  7. customA second crop of crystals is obtained from mother liquors, mp 75°-77° C.

Sources & evidence

ORD record
ord-f1b9a3e2ae364c8091ae3f6884792032
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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