Benzyl Alcohol → Benzyl bromoacetate

HRID 1112598Notes

Reaction equation

HRID 1112598 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[Br-:6].[K+].S(=O)(=O)(O)O.[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.O>[Br:6][CH2:2][C:3]([O:5][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 300Chloroacetic AcidHCID 1118Sulfuric AcidHCID 253877Potassium Bromide

Product 1

HCID 62576Benzyl bromoacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

94.5g (1 mol) of chloroacetic acid, 154.7g (1.3 mol) of potassium bromide, 127.4g (1.3 mol) of c.-sulfuric acid, 75 ml of water, 200g of toluene and 108g (1 mol) of benzylalcohol were used and treated in a similar way as described in Example 3. 214g (93.4% of theory) of benzyl bromoacetate were obtained. Bp. = 145° C/ 4 mmHg. 176.5g (99.7%) of potassium hydrogen sulfate was isolated.

Workup

  1. additiontreated in a similar way

Sources & evidence

ORD record
ord-9343f840880b4756888adaeaffa633dc
Source dataset
uspto-grants-1978_10
Patent number
US04123443

Reaction notes

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