Hydroxyphenylacetic acid → HCID 53677170, compound

HRID 1464626Notes

Reaction equation

HRID 1464626 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.[CH3:12][CH:13]1[CH2:18][C@H:17](O)[C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH:15]2[CH:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14]2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 6101p-Toluenesulfonic acidHCID 12285346HCID 12285346, compound

Product 1

HCID 53677170HCID 53677170, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.9 kg of p-hydroxyphenylacetic acid and 1.95 kg of (+)-menthol are heated to boiling for 16 hours with 40 g of p-toluenesulphonic acid in 25 l of toluene; about 300 ml of water are separated in this process. The toluene solution is washed with 10 l of saturated NaHCO3 solution and 10 l of water and concentrated to dryness in vacuo. The title compound is obtained as 5.4 kg of oily residue (98-100% of theory) having a purity of 91.8% (HPLC surface area percentage). For analytical purposes, the (+)-menthylhydroxyphenylacetate was recrystallised twice from n-hexane.

Workup

  1. customabout 300 ml of water are separated in this process
  2. washThe toluene solution is washed with 10 l of saturated NaHCO3 solution and 10 l of water
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a3371580324e4c62805ec8c83b39bf56
Source dataset
uspto-grants-1994_04
Patent number
US05306820

Reaction notes

Loading…