Hydroxyphenylacetic acid → Benzyl 2-(4-hydroxyphenyl)acetate

HRID 1886212Notes

Reaction equation

HRID 1886212 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Li+].[Li+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 7498Benzyl BromideHCID 11125Lithium Carbonate

Product 1

HCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Hydroxyphenylacetic acid (2.0 kg) is dissolved in DMF (8 L) and lithium carbonate (1.07 kg) is added in one portion followed by benzyl bromide (1.88 L). The mixture is heated to 100° C. over 1 hour, aged for 3 hours. The mixture is cooled to 85° C. and transferred into a 50 L vessel and quenched with 2N HCl (10 L).

Workup

  1. temperatureThe mixture is cooled to 85° C.
  2. customtransferred into a 50 L vessel
  3. customquenched with 2N HCl (10 L)

Sources & evidence

ORD record
ord-7c62da3dad8646539173a97f038bf291
Source dataset
uspto-grants-1992_09
Patent number
US05149838

Reaction notes

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