4-Hydroxybenzoic Acid → 4-(Octyloxy)benzoic acid

HRID 847681Notes

Reaction equation

HRID 847681 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CS(C)=O.[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>[OH-].[Na+]>[CH2:15]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 81401-Bromooctane

Product 1

HCID 172314-(Octyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of p-hydroxybenzoic acid (19.2 g, 150 mmoles) in 10% aqueous sodium hydroxide (120 ml) is added to dimethyl sulfoxide (DMSO) (480 ml) previously heated to 80° C. n-Octyl bromide (28.95 g, 150 mmoles) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml). Conc. hydrochloric acid (30 ml) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. mp 97°-99° C.

Workup

  1. additionis added dropwise to the solution
  2. customto stand until precipitation
  3. customThe precipitate is collected
  4. customdried
  5. customcrystallized from acetonitrile-water

Sources & evidence

ORD record
ord-2588e2a6d913424fae2b64d02b5ce5fd
Source dataset
uspto-grants-1981_10
Patent number
US04293482

Reaction notes

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