Chloroacetic Acid → [2-(Hexadecyloxy)-1-(hydroxymethyl)ethoxy]acetic acid

HRID 35959Notes

Reaction equation

HRID 35959 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([OH:7])=[O:6].[CH2:8]([O:24][CH2:25][CH:26]([OH:50])[CH2:27][O:28]C(C1C=CC(OC)=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O>C1(C)C=CC=CC=1>[CH2:8]([O:24][CH2:25][CH:26]([CH2:27][OH:28])[O:50][CH2:4][C:5]([OH:7])=[O:6])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 962WaterHCID 24758Sodium hydrideHCID 142607721-(Hexadecyloxy)-3-((4-methoxyphenyl)diphenylmethoxy)-2-propanol

Product 1

HCID 19939581[2-(Hexadecyloxy)-1-(hydroxymethyl)ethoxy]acetic acidYield 53.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a suspension of 13.1 g of 50% sodium hydride in 200 ml of toluene was add a solution of 12.6 g of chloroacetic acid in 50 ml of toluene over a 45 minute period. A solution of 65.5 g of 1-(hexadecyloxy)-3-[(4-methoxyphenyl)diphenylmethoxy]-2-propanol in 100 ml of toluene was added over 30 minutes. The mixture was refluxed for 65 hours, poured into water and acidified to pH 4. The mixture was extracted with ether. The ether solution was dried and evaporated. The residue was purified by chromatography giving 22.3 g of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 65 hours
  2. extractionThe mixture was extracted with ether
  3. dry with materialThe ether solution was dried
  4. customevaporated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-3bf2f62527dc456daf81f73f71e42290
Source dataset
uspto-grants-1995_05
Patent number
US05411983

Reaction notes

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