Sodium Hydroxide → HCID 19359215, compound

HRID 376799Notes

Reaction equation

Cl[O-:2].[Na+].[OH-].[Na+].[C:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH3:20])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)(=[O:8])C>>[C:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:19][CH3:20])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)([OH:8])=[O:2]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 19359190HCID 19359190, compound

HCID 23665760Sodium Hypochlorite

Product 1

HCID 19359215HCID 19359215, compoundYield 95%

Conditions

Temperature: 55 °C

Procedure

Part D--To a solution of sodium hypochlorite (330 mL, 17.32 g, 0.234 mol) in a solution of sodium hydroxide (50%, 172 mL), warmed to 55° C., was added, portionwise as a solid, 4-acetylphenylbutyric acid (16.0 g, 0.078 mol) while keeping the temperature between 60-70° C. All was stirred at 55° C. over 20 hours. The cooled solution was quenched by the dropwise addition of a solution of sodium bisulfite (25%, 330 mL). The mixture was then transferred to a beaker and acidified by the careful addition of concentrated hydrochloric acid. The resulting solid was collected, washed with water and dried, then triturated sequentially with chlorobutane and hexane to give 4-carboxyphenylbutyric acid (15.31 g, 0.074 mol, 95%) as a white solid. mp=190-195° C.; 1H NMR (DMSO) d 12.55 (bs, 1H), 8.1 (s, 1H), 7.85 (d, 2H, J=8.1 Hz), 7.3 (d, 2H, J=8.1 Hz), 2.7 (t, 2H, J=7.5 Hz), 2.2 (t, 2H, J=7.4 Hz), 1.8 (quintet, 2H, J=7.5 Hz).

Workup

custombetween 60-70° C
customThe cooled solution was quenched by the dropwise addition of a solution of sodium bisulfite (25%, 330 mL)
additionacidified by the careful addition of concentrated hydrochloric acid
customThe resulting solid was collected
washwashed with water
customdried
customtriturated sequentially with chlorobutane and hexane

Sources & evidence

ORD record: ord-03ab81514b8f4496b508e2093406c3e9
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022523

Reaction notes

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