Benzoic Acid → 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

HRID 1659619Notes

Reaction equation

HRID 1659619 reaction equation
[C:1]([OH:9])(=O)[C:2]1C=C[CH:5]=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH2:17][OH:18])=[CH:13][CH:12]=1.O1C=CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)Cl>[O:9]1[CH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[O:18][CH2:17][CH2:16][O:15][C:14]1[CH:19]=[CH:20][C:11]([Br:10])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 128104732-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The starting benzoic acid (I) is made by the reaction of 2-(4-bromophenoxy)ethanol (V) with dihydropyran, in the presence of methylene chloride and p-toluenesulfonic acid.H2O, to give 4-(2-tetrahydropyranyloxyethoxy)bromobenzene (VI). The bromobenzene (VI) is converted to 4-(2-tetrahydropyranyloxyethoxy)benzoic acid (VII) by reacting with magnesium, in tetrahydrofuran and dibromoethane, and then with carbon dioxide. Reaction of (VII) with methanol yields the starting benzoic acid (I). ##STR2##

Sources & evidence

ORD record
ord-2c9c154649684e9d9887963d5c835fe2
Source dataset
uspto-grants-1981_12
Patent number
US04304924

Reaction notes

Loading…