Chloroacetic Acid → 2-Butoxyethyl bromoacetate

HRID 1112599Notes

Reaction equation

HRID 1112599 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[Br-:6].[K+].S(=O)(=O)(O)O.[CH2:13]([O:17][CH2:18][CH2:19]O)[CH2:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1.O>[Br:6][CH2:2][C:3]([O:5][CH2:19][CH2:18][O:17][CH2:13][CH2:14][CH2:15][CH3:16])=[O:4]

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 1118Sulfuric AcidHCID 81332-ButoxyethanolHCID 253877Potassium Bromide

Product 1

HCID 130538312-Butoxyethyl bromoacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

94.5g (1 mol) of chloroacetic acid, 142.8g (1.2 mol) of potassium bromide, 117.6g (1.2 mol) of sulfuric acid, 75 ml of water, 200g of toluene and 118.1g (1 mol) of ethylene glycol butyl ether were used and treated in a similar way as described in Example 3. 225.1g (94.1% of theory) of 2-n-butoxyethyl bromoacetate were obtained. Bp. = 123° ~ 124° C/3 mmHg, nD25 = 1.4572, D420 = 1.6450. 161.4g (98.9%) of potassium hydrogen sulfate was isolated.

Workup

  1. additiontreated in a similar way

Sources & evidence

ORD record
ord-75c797759248436e996a630158d9aa2e
Source dataset
uspto-grants-1978_10
Patent number
US04123443

Reaction notes

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